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Salicylic acid, a natural product extract from Willow bark, well known as an antiinflammatory inhibitor of cyclooxygenase activity.
Synonyms: 2-Hydroxybenzoic acid; NSC 180
4.5
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Polyfluorinated salicylic acid analogs do not interfere with siderophore biosynthesis
Hegde, Pooja ; Orimoloye, Moyosore O. ; Sharma, Sachin ; Engelhart, Curtis A. ; Schnappinger, Dirk ; Aldrich, Courtney C.
Abstract: Tuberculosis (TB), caused by Mycobacterium tuberculosis (Mtb) is a leading cause of infectious disease mortality. The salicylic acid derived small mol. siderophores known as mycobactins are essential in vivo for iron acquisition of Mtb where iron is restricted in the host. Herein, we synthesize and explore the mechanism of action of polyfluorinated salicylic acid derivates, which were previously reported to possess potent antimycobacterial activity. We hypothesized fluorinated salicylic acid derivates may inhibit mycobactin biosynthesis through initial bioactivation and conversion to downstream metabolites that block late steps in assembly of the mycobactins. Enzymic studies demonstrated that some of the fluorinated salicylic acid derivatives compounds were readily activated by the bifunctional adenylating enzyme MbtA, responsible for incorporation of salicylic acid into the mycobactin biosynthetic pathway; however, they did not inhibit mycobactin biosynthesis as confirmed by LS-MS/MS using an authentic synthetic mycobactin standard Further mechanistic anal. of the most active derivative (Sal-4) using an MbtA-overexpressing Mtb strain as well as complementation studies with iron and salicylic acid revealed Sal-4 cannot be antagonized by overexpression of MbtA or through supplementation with iron or salicylic acid. Taken together, our results indicate the observed antimycobacterial activity of polyfluorinated salicylic acid derivative is independent of mycobactin biosynthesis.
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CAS No. : | 69-72-7 |
Formula : | C7H6O3 |
M.W : | 138.12 |
SMILES Code : | OC1=CC=CC=C1C(O)=O |
Synonyms : |
2-Hydroxybenzoic acid; NSC 180
|
MDL No. : | MFCD00002439 |
InChI Key : | YGSDEFSMJLZEOE-UHFFFAOYSA-N |
Pubchem ID : | 338 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H302-H318-H361 |
Precautionary Statements: | P201-P202-P264-P270-P280-P301+P312+P330-P305+P351+P338+P310-P308+P313-P405-P501 |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With chlorosulfonic acid; | EXAMPLE 1 Synthesis of 5-chlorosulfonylsalicylic acid To 125 ml of chlorosulfonic acid in a round bottom flask, cooled with an ice bath, was slowly added 25 g. of salicylic acid with constant stirring. After all the salicylic acid was dissolved the cool mixture was heated in an oil bath, at 75 C. under constant stirring, for about 1 hour. The heated mixture was then carefully poured onto about 500 g. of crushed ice forming a white solid. The white solid was collected in a Buchner funnel and was recrystallized from CH2 Cl2 to provide a 60% yield of a product having a melting point of 170-172 C. and identified as 5-chlorosulfonylsalicylic acid. |
With chlorosulfonic acid; at 0 - 70℃; for 3h; | EXAMPLE A5; 2-Cyclopentyloxy-5-methylsulfamoyl-benzoic acid; (a) 5-Chlorosulfonyl-2-hydroxy-benzoic acid; To 3.26 mol chlorosulfonic acid at 0 C. was added 652 mmol salicylic acid in small portions, and the mixture was then allowed to stir at RT for 1 h, then at 50 C. for 1 h, and finally at 70 C. for 1 h. The mixture was then added dropwise to 1000 ml ice-water with stirring and stirring continued for an additional 30 min. The ensuing white crystals were collected by filtration, washed three times with water, and then dried in vacuo at 45 C. for 16 h to yield the title compound. | |
With chlorosulfonic acid; at 0 - 70℃; for 3h; | (a) 5-Chlorosulfonvl-2-hvdroxv-benzoic acid; To 3.26 mol chlorosulfonic acid at 0 0C was added 652 mmol salicylic acid in small portions and the mixture was then allowed to stir at RT for 1 h, then at 50 0C for 1 h, and finally at 70 0C for 1 h. The mixture was then added dropwise to 1000 ml ice-water with stirring and stirring continued for an additional 30 min. The ensuing white crystals were collected by filtration, washed three times with water, and then dried in vacuo at 45 0C for 16 h to yield the title compound. MS (m/e): 236.8 ([(37Cl)M-H]", 33%), 235.0 ([{37C1}M- H]", 100%) |
With chlorosulfonic acid; at 20 - 70℃; for 3h; | EXAMPLE B13 2-Methoxy-5-methylsulfamoyl-benzoic acid (a) 5-Chlorosulfonyl-2-hydroxy-benzoic acid; To 3.26 mol chlorosulfonic acid at 0 C. was added 652 mmol salicylic acid in small portions and the mixture was then allowed to stir at RT for 1 h, then at 50 C. for 1 h, and finally at 70 C. for 1 h. The mixture was then added dropwise to 1000 ml ice-water with stirring and stirring continued for an additional 30 min. The ensuing white crystals were collected by filtration, washed three times with water, and then dried in vacuo at 45 C. for 16 h to yield the title compound. MS (m/e): 236.8 ([{37Cl}M-H]-, 33%), 235.0 ([{37Cl}M-H]-, 100%) | |
With chlorosulfonic acid; thionyl chloride; at 0 - 25℃; for 15.9167h; | Example 1Preparation of 2- hydroxy-5-(4 methyl)-l-piperazinyl sulphonyl) benzoic acid Step-1: Preparation of 5-Chlorosulfonyl-2-hydroxy benzoic acidTo the chilled chlorosulfonic acid (1012 g), salicylic acid (200 g) was added at 0-50C over a period of 1 hour 40 min. The temperature of the reaction mixture was maintained at 20-250C for 2 hrs. Then thionyl chloride (172.4 g) was added over a period of 15 min and maintained for 12 hrs. The product formed was poured onto ice and maintained for lhr. The product was filtered and washed with DM water to get 5-Chlorosulfonyl-2- hydroxy benzoic acid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | Xvlene (150 mL) and salicylic acid (1) (100 g, 0,072 mol) were added to a 500 mL, 4 necked round-bottom flask equipped with a mechanical stirrer and thermocouple. Thion I chloride (87 g, 0.036 mol)) was added at 10C to 15C. After addition of thionyl chloride, the reaction mass was stiired at 10C to 15C for 30 minutes, The reaction mass was further heated at 35C-40C for 1 hr. A solution of salicylamide (2) (100 g, 0.072 mol) in 200 mL of xylene was added to the reaction mass at 25C to 30C. After addition, the reaction mass was gradually heated at 80C to 120C and stirred for 2 hrs, After completion of reaction, excess of xvlene was removed under vaccum. Methanol 200 mL was added to the reaction mass at 70C to 80C and stirred for 1 hour. The reaction mass was cooled gradually at 25C to 30C. The solid was filtered and washed with methanol and dried at 55C to 60C under vacuum tray drier to yield 165 g 2-(2-hvdroxyphenvI)-4- 1 ,3-benzoxazin-4-one (3). Yield 95%, rn.p. 239C. LCMS: m/z = 240.22 (M+H) calcd, for C14H9N30: 239.2. | |
76% | With pyridine; thionyl chloride; In 5,5-dimethyl-1,3-cyclohexadiene; at 20℃;Reflux; | Salicylic acid (6.04 g, 43.75 mmol), salicylamide (5.00 g, 36.46 mmol) and pyridine (0.37 mL, 4.63 mmol) were heated at reflux in xylene (18.00 mL) for 15 min. Thionyl chloride (5.83 mL, 80.21 mmol) was added with vigorous stirring over a period of 4 h, with further stirring for 16 h at room temperature. Xylene was removed by concentration in vacuo, and resulting solid residue was suspended in ethanol (15.00 mL) and acetic acid (0.36 mL). The mixture was heated to reflux and cooled to room temperature. The solid precipitate was isolated and dried to yield 2-(2-Hydroxyphenyl)-benzo-4H-[1,3]-oxazin-4-one (1) (6.59 g, 27.54 mmol, 76%) as yellow solid. |
54% | With 1,3,5-trichloro-2,4,6-triazine; triethylamine; In toluene; at 80℃; for 16h;Dean-Stark; Inert atmosphere; | In a round bottom flask fitted a reflux condenser and a Dean-Stark trap, a suspension of salicylic acid (27.6 g, 0.2 mol), salicylamide (23.3 g, 0.17 mol) and 2,4,6-trichloro-1,3,5-triazine (24.8 g, 0.134 mol) in 600 mL toluene was heated under a nitrogen atmosphere for 30 minutes at 80C. Then triethylamine (28.08 mL, 0.2 mol) was added slowly to the solution and the resulting mixture was heat to reflux for 16 h. Precipitation of some solid began to occur during the reaction; the reaction mixture was cooled to about 80C and then filtered hot (by suction) as quickly as possible to remove the solid mixture of triethylamine hydrochloride, cyanuric acid and other solids. The filtrate was then evaporated and the resulting crude solid was recrystallized39 from ethanol (600 mL) to give21.9 g (54% yield) of benzoxazinone 4 in better than 98% purity as a very pale yellow solid. All spectroscopic data of product 4 matched those of an authentic sample. |
43% | With pyridine; thionyl chloride; In N,N-dimethyl-formamide; for 4h;Reflux; | Salicylic acid (II) (2g, 14.5mmol), salicylamide (III) (1.53g, 11.1mmol) and N, N-dimethylformamide (1ml) were added to the solvent xylene (20ml), heated Reflux and mix well.After adding thionyl chloride (1.9 g, 16.0 mmol), it was stirred well for 4 h.A large amount of HCl and SO2 gas are generated during the reaction, and a tail gas absorption device is used. After a period of reaction, crystals were precipitated and stirring was continued for 30 min. After completion of the reaction, the mixture was distilled under reduced pressure, and the solvent was evaporated. The solid was washed with a mixed solution of ethanol (30 ml) and acetic acid (1 ml) and recrystallized from 2-methoxyethanol.The yellow-green solid product IV (1.14 g, 4.78 mmol, 43%) was obtained. |
39.3% | Example 1 Preparation of 2-(2-hydroxyphe41)-benz[1,3]oxazin-4-one A mixture of dichloromethane (200 ml), salicylic acid (50.0 gm) and p-toulenesulfonyl chloride (69 gm) were cooled to 10-15 C. Diisopropyl ethyl-amine (139.0 ml) was added drop-wise to the above mixture at 10-20 C. Reaction mass was stirred for 10 min at 10-20 C. and raised the temperature to 25-30 C. The reaction was maintained for 2 hours at 25-30 C. Reaction mass was cooled 0-5 C. Purified water (200 ml) was charged to the above mixture and stirred for 15 minutes. The layers were separated. Salicylamide (39.6 gm) and toluene (200.0ml) were heated to 85-90 C. and the above organic layer was added drop-wise into salicyliamide solution with simultaneous distillation of solvent at 85-90 C. and distilled the solvent upto the reaction mass temperature reaches to 110-120 C. and further reaction was maintained for 3hrs at 110-120 C. Further solvent was distilled under atmospheric pressure upto reaction mass temperature reaches to 140-160 c and further the reaction was maintained for 1-2 hrs at 140-160 C. until the starting material disappears. Reaction mass was cooled to 75-80 C. and distilled off completely toluene under vacuum. Ethanol (50 ml) was added to the above reaction mass at 75-80 C. Reaction was stirred for 15 min and distilled off the ethanol at 75-80 C. Further ethanol (50.0 ml) was added stir for 5-10 min. Ethanol was distilled off completely under vacuum at 75-80 C. Ethanol (150 ml) was charged into above contents at 75-80 C. The contents were maintained for 1 hour at 75-80 C. and slowly cooled to 0-5 C. Reaction mass was maintained for 2 hrs at 0-5 C. The reaction mass was filtered and washed with ethanol (50.0 ml). Dried the compound at 50-55 C. Yield: 39.30%. | |
39% | With pyridine; thionyl chloride; In 5,5-dimethyl-1,3-cyclohexadiene; ethanol; for 4h;Reflux; | Salicylic acid (2 g, 14.5 mmol), salicylamide (1.53 g, 11.1 mmol)and pyridine (1 ml) were refluxed in xylene (20 mL). Thionylchloride (1.9 g, 16.0 mmol) was added with vigorous stirring over aperiod of 4 h. An intense evolution of SO2 and HCl was noted. At theend of the reaction, the product started to crystallize. Stirring wascontinued for an additional 30 min, and the xylenewas removed byreduced-pressure distillation. The resulting solid residue was suspendedin EtOH (30 mL) and acetic acid (1 mL). The mixture washeated gently and then allowed to cool to 20 C. The precipitatewasfiltered and recrystallized from 2-methoxyethanol (35 mL). Yield:yellow-green solid (1.04 g, 4.34 mmol, 39%). m.p. 202.2e204.6 C.1H NMR (500 MHz, DMSO-d6) d12.95 (s, 1H), 8.25e8.21 (m, 1H),8.08 (dd, J1 7.8, J2 1.5 Hz, 1H), 7.98e7.94 (m, 1H), 7.81 (dd,J1 8.4, J2 0.6 Hz, 1H), 7.68e7.60 (m, 2H), 7.13e7.08 (m, 2H). ESIMS:m/z. Calculated for C14H9NO3 239.06; found[MH] 240.0655. |
With pyridine; thionyl chloride; In xylene; for 11h;Reflux;Product distribution / selectivity; | Mixture of salicylic acid (100 grams), salicylamide (89.3 grams), pyridine (15.2 ml) and xylene (600 ml) was heated to reflux temperature. Thionyl chloride (100.5 ml) was added to the above mixture at reflux temperature for 3 hours. Intense evolution of SO2 and hydrochloric acid was observed, the reaction mixture was then stirred for 8 hrs. Xylene was removed from the reaction mixture by distillation under reduced pressure. The resulting residue was suspended in methanol (200 ml) and raised the temperature to 60-65C. The reaction mixture was stirred for one hour at 60-65C and cooled to 0-5C and further stirred' for one hour. The solid obtained was filtered, washed with methanol and dried to get the title compound.Yield: 130 grams | |
Example 1; Preparation of 2-(2-Hydroxyphenyl)-4H-1,3-benzoxazine-4-oneSalicylic acid (50 gm) was taken in xylene (250 ml) followed by the addition of thionyl chloride (64.5 gm) drop wise to the reaction mixture at 25-30 C. The reaction mixture was stirred for 90 minutes at 40-45 C. The excess thionyl chloride was removed by distillation. Salicylamide (49.7 gm) was added to the resulting mixture and followed by the distillation of xylene up to a reaction temperature of 170 C. The reaction mixture was further stirred for 60 minutes at 80 C. followed by the addition of ethanol (80 ml) and refluxed for 15 minutes. The resulting mass was cooled to 25 C. and stirred for 30 minutes at the same temperature. The resulting solid was filtered and dried to produce 43 gm of 2-(2-hydroxyphenyl)-4H-1,3-benzoxazine-4-one as slightly yellow crystals. (Melting point: 206-208 C.). | ||
Example-I [68] Preparation of 2-(2-hydroxyphenyl) benz [e] [1, 3] oxazin-4-one [69] [70] Xylene (1.5 L) and salicylic acid (1 Kg.) was added to a 5 L 4-neck round bottom flask equipped with a mechanical stirrer and thermocouple. Thionyl chloride (1.29 kg) was added at 10 oC to 15oC. After addition of thionyl chloride reaction mass is stirred at 10 0C to 15oC for 30 minutes. Reaction mass is heated at 35-40 0C for 1 hr. Salicylamide solution (0.891 kg in 2.0 lit of Xylene) was added in reaction mass at 25 0 C -30 0 C. After addition reaction mass was gradually heated at 80 0C - 126 0C and stirred for 2 hrs. After the completion of reaction excess of Xylene was distilled out. Methanol was added in the reaction mass at 70 0C -80 0C and stirred for 1 hr. gradually cooled the reaction mass at 25-30 0C. Filtered the solid and washed with Methanol and sucked it dry. Dry the obtained solid at 55-60 0C under vacuum tray drier. | ||
EXAMPLE-I Preparation of 2-(2-Hydroxyphenyl) Benz [e] [1, 3] Oxazin-4-One Xylene (1.5 L) and salicylic acid (1 Kg.) was added to a 5 L 4-neck round bottom flask equipped with a mechanical stirrer and thermocouple. Thionyl chloride (1.29 kg) was added at 10 C. to 15 C. After addition of thionyl chloride reaction mass is stirred at 10 C. to 15 C. for 30 minutes. Reaction mass is heated at 35-40 C. for 1 hr. Salicylamide solution (0.891 kg in 2.0 lit of Xylene) was added in reaction mass at 25 C.-30 C. After addition reaction mass was gradually heated at 80 C.-126 C. and stirred for 2 hrs. After the completion of reaction excess of Xylene was distilled out. Methanol was added in the reaction mass at 70 C. -80 C. and stirred for 1 hr. gradually cooled the reaction mass at 25-30 C. Filtered the solid and washed with Methanol and sucked it dry. Dry the obtained solid at 55-60 C. under vacuum tray drier. | ||
With pyridine; thionyl chloride; In 5,5-dimethyl-1,3-cyclohexadiene;Reflux; | Salicylic acid (b) 24.9 g was sequentially added to a 250 mL three-necked flask. Salicylamide (c) 20.6g, 1.5 mL of pyridine and 30 mL of xylene, Slowly add 23.7 mL of thionyl chloride under stirring. After heating and refluxing, The solvent was removed under reduced pressure. The residue is dissolved by heating with a mixed solvent of ethanol and acetic acid. cool down, filter, Ethylene glycol monomethyl ether recrystallized, Yellow needle crystals, Mp 226-227 C. | |
15 g | With pyridine; aluminum (III) chloride; thionyl chloride; In o-xylene; at 25 - 125℃; for 1.5h; | 10 grams of salicylamide, 10.90 grams of salicylic acid, 0.20 grams aluminum chloride and 1.17 grams pyridine were added to 55 ml o-xylene at 25-30C. Reaction mass temperature was raised to 115-125C and then 16.70 grams thionyl chloride was slowly added over a period of 60 min at 1 15-125C and maintained at 1 15-125C for 30 min. The reaction mass was cooled to 25-30C and further added 33 ml absolute alcohol. The obtained slurry product was filtered and washed with absolute alcohol to give 15 grams of pale yellow crystalline 2-(2- hydroxyphenyl)-4H- l,3-benzoxazin-4-one having chromatographic purity about (0077) 95.5 %. (0078) The above product was purified by refluxing in absolute alcohol in presence of sodium methoxide followed by glacial acetic acid addition and then cooled to room temperature. The product was filtered and washed with absolute alcohol to obtain pure 2- (2-hydroxyphenyl) -4H- 1 , 3 -b enzoxazin-4-one having chromatographic purity about 99.5 %. |
With pyridine; thionyl chloride; In 5,5-dimethyl-1,3-cyclohexadiene; at 130 - 140℃; for 2h; | General procedure: Substituted benzoic acid (1.2e2.0 g, 10 mmol) and o-hydroxybenzamide (1.5e2.3 g, 11 mmol) were added into 20 mL of xylene,then anhydrous pyridine (catalytic amount) was added, and thionylchloride (1.5 mL, 20 mmol) in xylene (8 mL) was added dropwiseover 30 mins at room temperature. After that, stirring was undertakenat 130e140 C. The mixturewas stirred for 2 h (TLC show acidwas consumed) and the solvent was distilled off under reducedpressure to obtain intermediate. The intermediate, 4-hydrazinobenzene-1-sulfonamide hydrochloride (1.1 g, 5 mmol)and triethylamine (1.0 g,10 mmol), were added to 15 mL of absoluteethanol, and the mixture was stirred at 80 C for 18 h. When thereaction was complete, the solution was filtered, and saturatedsodium bicarbonate was added to adjust pH to 7. The solution wasextracted with ethyl acetate, and the organic layer was washedwith 20 mL of saturated brine and dried over anhydrous sodium.The solvent was evaporated under reduced pressure to obtain thetarget compounds. The target compounds were recrystallized frommethanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57 - 70% | A mixture of <strong>[51997-51-4]4-(oxiran-2-ylmethoxy)-9H-carbazole</strong> (II) (25.0 g, 104.60 mmole) and 62. 5 ml-2-propanol is heated to 70C to 80C. To this 2- (2- methoxyphenoxy) ethylamine (III) (20.96 g, 125.52 mmole) is added in one lot. The temperature of the reaction mass is raised to 80C to 85C and refluxed for 1.0 hour. The reaction mixture is added into the preheated (80C to 85C) solution of salicylic acid (18.77 g, 135.98 mmoles) in 187.5 ml 2-propanol. This reaction mass is further refluxed for 2.0 hours, cooled to 50C to 55C and stirred for one hour at this temperature. The solid is filtered followed by three 33 ml wash with hot (50C to 55C) 2-propanol. The wet product dried at 60C to 65C for 6 hours or till constant weight gives 32.5 g (Yield=57%) of Carvedilol salicylate, which contains about 2-2.5 % of compound (IV) as an impurity. HPLC Purity = 92. 5-95. 0 % Melting point. = 164C-166C; Example: 2; Preparation of Carvedilol salicylate : A mixture of 4- (oxiran-2-ylmethoxy)-9H-carbazole (II) (25.0 g, 104.60 mmole) and 62.5 ml 2-propanol is heated to 70C to 80C. To this 2- (2- methoxyphenoxy) ethylamine (III) (25.33 g, 151. 67 mmole) is added in one lot. The temperature of the reaction mass is then raised to 80C to 82C and refluxed for 1 hour. The reaction mixture is added into the preheated (80C to 85C) solution of salicylic acid (18.77 g, 135.98 mmoles) in 187.5 ml of 2-propanol. The reaction mass is further refluxed for 2 hours, cooled to 50C to 55C and stirred for 1 hour at this temperature. The solid is filtered, followed by three 33 ml wash with hot (50C to 55C) 2-propanol. The wet product dried at 60C to 65C for 6 hours or till constant weight gives 39.75 g (Yield 70%) of Carvedilol salicylate, which contains about 2-2.5 % of compound (IV) as an impurity. HPLC purity = 92. 5-95% Melting point = 164C-166C; Example: 3; Process of purification for Carvedilol salicylate : A mixture of Carvedilol salicylate (39.0 g 39.81 mmole) and ethyl acetate (312 ml) is stirred at 70C to 75C for 30 minutes then cooled to 50C to 55C and stirred at that temperature for 1 hour. The content is filtered at same temperature and washed with hot (50C to 55C) ethyl acetate, the product is dried at 60C to 65C for 6 hours or till constant weight to afford 37.0 g of pure Carvedilol salicylate (Recovery=94.87%), which contains about 1.0-2. 0 % of compound (IV) as an impurity. HPLC purity = 94-97 % Melting point = 165C-167 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With 1H-imidazole; dicyclohexyl-carbodiimide; In ethyl acetate; at 0 - 20℃; | To a solution of tert-butyl 2-aminopropylcarbamate (3.6 g, 20.6 mmol), 2-hydroxybenzoic acid (2.79 g, 20.6 mmol) and imidazole (1.41 g, 20.6 mmol) in EtOAc (100 mL) at 0° C. was slowly added a solution of DCC (4.26 g, 20.6 mmol) in EtOAc (50 mL). The reaction mixture was stirred (RT, 16 h), filtered and concentrated under reduced pressure. The crude product was purified by silica chromatography, EtOAc/Petroleum ether (0-20percent) to afford tert-butyl 2-(2-hydroxybenzamido)propylcarbamate (2.4 g, 40percent) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE Il; Preparation of Carvedilol salicylate; To a solution of lOOg of 4-(2,3-epoxypropoxy) carbazole (III) in isopropyl alcohol (200 ml) at 10-300C, 2-(2-methoxyphenoxy) ethylamine (125 g) was added and the reaction mixture is stirred at 75-800C for reaction completion. Reaction mass is cooled and <n="12"/>added to a solution of salicylic acid (90- g) in isopropyl alcohol. Mass is refluxed to get ?precipitation. Mass is cooled and product is filtered and washed with isopropyl alcohol. Solid is dried to get 160 g Carvedilol salicylate which can be optionally recrystallized. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | 6A-Deoxy-6A-((2-hydroxybenzoyl)amino)-beta-cyclodextrin. The synthesis was adapted from apreviously published method.15 Solutions of N,N'-dicyclohexylcarbodiimide (91 mg, 0.44 mmol)in DMF (4 mL) and hydroxybenzotriazole (68 mg, 0.44 mmol) in DMF (4 ml) were added to asolution of salicylic acid (61 mg, 0.44 mmol) in DMF (5 mL) cooled to 0 oC. The reactionmixture was stirred for 0.5 hours at 0 oC and a solution of 6A-deoxy-6A-amino- -cyclodextrin16,17 (500 mg, 0.44 mmol) in DMF (17 mL) was added dropwise. The reactionmixture was then stirred for another hour at 0 oC and 48 hours at room temperature. The reactionwas quenched by pouring the mixture into acetone (300 mL). The precipitate was filtered out andpurified by crystallization from water to yield 333 mg (60percent) of the title compound as a whitepowder. Mp 228 oC (decomp.). IR (KBr): 3507, 3280, 3155, 3117, 3058, 1642, 1150, 1030 cm-1.1H NMR (DMSO-d6): 12.39 (s, 1 H, Ar-OH), 8.67 (s, 1 H, -NH-), 7.82 (d, J 7.6 Hz, 1 H, Ar-H), 7.38 (t, J 7.7 Hz, 1H, Ar-H), 6.94?6.82 (m, 2 H,Ar-H), 5.94?5.51 (m, 14 H, 7 x CD-OH (2),7 x CD-OH (3)), 4.95?4.75 (m, 7 H, 7 x CD-H (1)), 4.56?4.33 (m, 6 H, 6 x CD-OH (6)), 3.92-3.10 (m, 42 H, 7 x CD-H (2), 7 x CD-H (3), 7 x CD-H (4), 7 x CD-H (5), 14 x CD-H (6)) ppm.13C NMR (DMSO-d6): = 168.61 (-CONH-), 159.65 (Ar-C-OH),133.52(Ar-C), 128.15(Ar-C),118.51(Ar-C), 117.21(Ar-C), 115.56(Ar-C), 102.39?101.88 (7 x CD-C (1)), 84.16?59.91 (7xCDC(2), 7 x CD-C (3), 7 x CD-C (4), 7 x CD-C (5), 7 x CD-C (6)) ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3.25g | at 20℃; for 1h; | 1.87 g (10mmo1) of 3-(2-ethylhexyloxy) propylamine and the salicylic acid 1.38g (10mmol) were measured, respectively, and it taught the reaction container. Contents were stirred and mixed at the room temperature for 1 hour, and 3.25 g of 3-(2-ethylhexyloxy) propyl ammonium salicylate (the chemical formula 9, an orange liquid) was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | With pyridine; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; copper(I) bromide; In para-xylene; at 120℃; for 36h;Schlenk technique; Green chemistry; | CuBr 6 mg (0.04 mmol), TEMPO 5 mg (0.03 mmol), compounded in a 25 mL Schlenk reaction tube<strong>[78581-99-4]5,6-difluorobenzimidazole</strong> 62 mg (0.4 mmol),28 mg (0.2 mmol) of salicylic acid (0.2 mmol) and p-xylene (0.5 mL), followed by 33 muL of pyridine (0.4 mmol) were added and the reaction was stirred at 120C for 36 hours under reflux.Cool to room temperature, transfer all to a 25 mL flask, spin off the solvent on a rotary evaporator, add an appropriate amount of silica gel to spin dry, and then use a 300-400 mesh silica gel column. The developing solvent used is petroleum ether:ethyl acetate=16: 1 to 6:1, that is, compound III-9 26mg, yield 48%; white solid |
Tags: 69-72-7 synthesis path| 69-72-7 SDS| 69-72-7 COA| 69-72-7 purity| 69-72-7 application| 69-72-7 NMR| 69-72-7 COA| 69-72-7 structure
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H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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