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[ CAS No. 723280-98-6 ] {[proInfo.proName]}

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Chemical Structure| 723280-98-6
Chemical Structure| 723280-98-6
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Product Details of [ 723280-98-6 ]

CAS No. :723280-98-6 MDL No. :MFCD12828220
Formula : C9H4BrClN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :KGTVATADCQABRD-UHFFFAOYSA-N
M.W : 287.50 Pubchem ID :21984361
Synonyms :

Calculated chemistry of [ 723280-98-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 63.27
TPSA : 58.71 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.68 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.81
Log Po/w (XLOGP3) : 3.34
Log Po/w (WLOGP) : 3.56
Log Po/w (MLOGP) : 1.93
Log Po/w (SILICOS-IT) : 1.54
Consensus Log Po/w : 2.44

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -4.15
Solubility : 0.0202 mg/ml ; 0.0000701 mol/l
Class : Moderately soluble
Log S (Ali) : -4.25
Solubility : 0.0162 mg/ml ; 0.0000562 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.54
Solubility : 0.00823 mg/ml ; 0.0000286 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 2.09

Safety of [ 723280-98-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 723280-98-6 ]

* 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.

  • Downstream synthetic route of [ 723280-98-6 ]

[ 723280-98-6 ] Synthesis Path-Downstream   1~16

  • 2
  • [ 723280-98-6 ]
  • [ 3218-02-8 ]
  • [ 723283-76-9 ]
YieldReaction ConditionsOperation in experiment
In dichloromethane; at 20℃; for 18h; Under a nitrogen atmosphere, cyclohexylmethylamine (40.9 ML, 315 mmol) was added dropwise to a solution of <strong>[723280-98-6]7-bromo-4-chloro-3-nitroquinoline</strong> (30.0 g, 105 mmol) in dichloromethane (524 mL). The reaction was stirred for 18 hours at ambient temperature and then concentrated under reduced pressure. Water (200 mL) was added to the residue, and the mixture was stirred for three hours. Acetonitrile was added; a precipitate formed. The solid was isolated by filtration, dried under a flow of air for two hours, and recrystallized from acetonitrile to provide 24.0 g of (7-bromo-3-nitroquinolin-4- yl) cyclohexylmethylamine as a yellow solid.
  • 3
  • [ 723280-98-6 ]
  • [ 68076-36-8 ]
  • [ 723281-79-6 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at 20℃; A solution OF TERT-BUTOXY N- (4-AMINOBUTYL) carbamate (15.38 g, 81.7 mmol) in dichloromethane (100 mL) was added dropwise over a period of 30 minutes to a solution of <strong>[723280-98-6]7-bromo-4-chloro-3-nitroquinoline</strong> (74.3 mmol) and triethylamine (20.6 mL, 149 mmol) in dichloromethane (400 mL), and the reaction was stirred overnight at ambient temperature. The reaction was diluted with dichloromethane (500 mL), washed sequentially with water and brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was recrystallized from isopropanol to provide TERT-BUTYL [4- (7-BROMO-3- NITROQUINOLIN-4-YLAMINO) butyl] carbamate as a yellow solid.
  • 4
  • [ 723280-98-6 ]
  • [ 107-15-3 ]
  • N1-(7-bromo-3-nitroquinolin-4-yl)ethane-1,2-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
A solution of <strong>[723280-98-6]7-bromo-4-chloro-3-nitroquinoline</strong> (143.8 g, 0.5 mol) in 800 mL warm DMF was added to a stirred solution of ethylenediamine in 200 mL DMF at room temperature; the reaction was stirred at room temperature overnight. The reaction was quenched with 2 L water and stirred for an additional hour. Additional water was added, and the mixture was stirred overnight. A precipitate formed and was isolated by filtration and air-dried overnight on the filter funnel to provide NL- (7-BROMO-3-NITROQUINOLIN-4- yl) ethane-1, 2-diamine as a yellow solid.
  • 5
  • [ 723280-98-6 ]
  • [ 24424-99-5 ]
  • [ 723283-32-7 ]
YieldReaction ConditionsOperation in experiment
A solution of <strong>[723280-98-6]7-bromo-4-chloro-3-nitroquinoline</strong> (140.00 g, 486.96 mmol) in chloroform (2.8 L) was cooled to 0 C. Triethylamine (82.0 mL, 588 mol) and ethylenediamine (35.75 ML, 535.6 mmol) were sequentially added; the resulting mixture was stirred for one hour at 0 C then allowed to warm to ambient temperature and stirred for two hours. Additional ethylenediamine (0.1 equivalent) was added, and the reaction was stirred for an additional 1.75 hours. Additional triethylamine (88.0 ML, 631 mmol) followed by a solution of di-tert- butyl dicarbonate (180.0 mL, 779.1 mmol) in chloroform (320 ML) were added, and the reaction was stirred overnight at ambient temperature. Water (750 mL) was added, and the mixture was stirred for 15 minutes. The organic layer was separated and washed with 1% aqueous sodium carbonate (2 x 750 mL), dried over sodium sulfate, filtered through a layer of CELITE filter aid, and concentrated under reduced pressure. The resulting solid was triturated with hot acetonitrile (5 mL/g at 95 C), cooled in an ice bath, and isolated by filtration to provide 165.0 G OF TERT-BUTYL [2- (7-BROMO-3-NITROQUINOLIN-4- ylamino) ethyl] carbamate as a light yellow solid.
  • 6
  • [ 723280-98-6 ]
  • [ 108468-00-4 ]
  • [ 723284-13-7 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; for 16h; 1- (N-BOC-AMINOMETHYL)-4- (AMINOMETHYL) benzene (5.0 g, 21 mmol) in dichloromethane (50 ML) was added dropwise to a mixture of 7-bromo-4- chloro-3-nitroquinoline (5.81 g, 20 mmol) and triethylamine (5.63 mL) in dichloromethane (60 mL). The reaction was stirred for 16 hours and then washed sequentially with water and saturated aqueous sodium chloride. The organic fraction was dried over sodium sulfate, filtered and concentrated to provide a yellow crystalline solid. Recrystallization from 2-propanol yielded 9.1 g of tert-butyl {4- [ (7-bromo-3-nitroquinolin-4- ylamino) methyl] benzyl} carbamate as a yellow powder.
  • 7
  • [ 723280-98-6 ]
  • [ 78-81-9 ]
  • [ 723281-00-3 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at 0 - 20℃; for 2h; 7-Bromo-4-chloro-3-nitroquinoline (33.5 g, 117 mmol) and Et3N (13.0 g, 128 mmol) were dissolved in CH2C12 (500 mL) and cooled on an ice bath. Isobutylamine (9.36 g, 128 mmol) was added in one portion and then the reaction was allowed to warm to room temperature. After 2 h, the reaction mixture was washed with water (500 mL), and the aqueous layer was extracted with CH2C12 (2 x 100 mL). The combined organic layers were dried over MGS04, filtered, and concentrated to afford 38.0 g of a yellow solid. Recrystallization from refluxing isopropanol (1.1 L) afforded 34.0 g of (7- bromo-3-nitroquinolin-4-yl) isobutylamine as yellow needles. 1H NMR (300 MHz, CDCl3) 8 9.79 (brs, 1H), 9.35 (s, 1H), 8.16 (d, J= 9.1 Hz, 1H), 8.16 (d, J= 2.2 Hz, 1H), 7.57 (dd, J = 9.1, 2.2 Hz, 1H), 3.75 (dd, J = 6.6, 5.0 Hz, 2H), 2.14-2. 01 (m, 1H), 1.10 (d, J= 6.9 Hz, 6H).
With triethylamine; In N,N-dimethyl-formamide; at 20℃; To a suspension of <strong>[723280-98-6]7-bromo-4-chloro-3-nitroquinoline</strong> (25.0 g, 87.0 mmol) in DMF (70 mL) was added triethylamine (18.2 mL,130 mmol). A solution of iso- butylamine (9.50mL, 95.7 mmol) in DMF (20 mL) was added dropwise. The viscous reaction mixture was stirred overnight at ambient temperature. Water (200 mL) was added and the mixture was stirred for 1 hour. A solid was isolated by filtration, washed with water, and dried in a vacuum oven overnight to yield 26.1 g of 7-bromo-N-(2-methylpropyl)-3-nitroquinolin-4-amine as a yellow powder.
With triethylamine; In N,N-dimethyl-formamide; at 20℃; Part E To a suspensionof <strong>[723280-98-6]7-bromo-4-chloro-3-nitroquinoline</strong> (25.0 g, 87.0 mmol) in DMF (70 mL) was added triethylamine (18.2 mL,130 mmol). A solution of iso- butylamine (9.50 mL, 95.7 mmol) in DMF (20 mL) was added dropwise. The viscous reaction mixture was stirred overnight at ambient temperature. Water (200 mL) was added and the mixture was stirred for1 hour. A solid was isolated by filtration, washed with water, and dried in a vacuum oven overnight to yield 26.1 gof 7-bromo-N-(2-methylpropyl)-3-nitroquinolin-4-amine as a yellow powder.
  • 8
  • [ 723280-98-6 ]
  • [ 723283-91-8 ]
  • [ 78-81-9 ]
  • [ 723281-00-3 ]
  • [ 723283-92-9 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at 20℃; for 0.5h; Under a nitrogen atmosphere, isobutylamine (11.0 ML, 0.111 mol) was added to the material from Part D and triethylamine (11.0 mL, 0.111 mol) in dichloromethane (15 mL). The reaction was stirred for 30 minutes at ambient temperature, and the volatiles were removed under reduced pressure to provide a 2: 1 mixture of (7-bromo-3-nitroquinolin-4-yl) isobutylamine and (5-bromo-3- nitroquinolin-4-yl) isobutylamine containing some triethylamine.
  • 9
  • [ 723280-94-2 ]
  • [ 723280-98-6 ]
YieldReaction ConditionsOperation in experiment
81% With trichlorophosphate; In N,N-dimethyl-formamide; at 120℃; for 3h;Inert atmosphere; 7-Bromo-3-nitroquinolin-4-ol (400, 3.8 g, 14.12 mmol) was suspended in POCb (20 mL). Anhydrous DMF (1 mL) was added. The mixture was then heated to 120C under an atmosphere of nitrogen for 3 hours at which time the reaction was cooled to room temperature. The precipitate was collected by filtration, washed with water, and then partitioned between CH2CI2 (60 mL) and a saturated aqueous solution of Na2C03. The organic layer was separated, washed with brine, dried over Na2S04, filtered, and concentrated to afford 3.3 g (1 1.5 mmol, 81%) of 7-bromo-4-chloro-3-nitroquinoline (401) as a beige-colored solid. (ES, m/z): [M+H]+ = 287.1 / 288.9.
81% With trichlorophosphate; In N,N-dimethyl-formamide; at 120℃; for 3h;Inert atmosphere; 7-Bromo-3-nitroquinolin-4-ol (3.8 g, 14.12 mmol) was suspended in POCh (20 mL). Anhydrous DMF (1 mL) was added. The mixture was then heated to 120C under an atmosphere of nitrogen for 3 hours at which time the reaction was cooled to room temperature. The precipitate was collected by filtration, washed with water, and then partitioned between CH2CI2 (60 mL) and a saturated aqueous solution of Na2C03. The organic layer was separated, washed with brine, dried over Na2S04, filtered, and concentrated to afford 3.3 g (11.5 mmol, 81%) of 7-bromo-4-chloro-3- nitroquinoline as a beige-colored solid. (ES, m/z): [M+H]+ = 287.1 / 288.9.
With trichlorophosphate; at 102℃; for 0.75h; 7-Bromo-3-nitroquinolin-4-ol (42 g, 156 millimoles (mmol)) was suspended in POC13 (130 ML) and brought to 102C under an atmosphere of N2. After 45 min, all of the solids had dissolved, so the reaction was cooled to room temperature (RT). The resulting solids were collected by filtration, washed with H2O, and then partitioned with CH2C12 (3 L) and 2M Na2C03 (500 mL). The organic layer was separated, washed with H20 (LX), dried over NA2S04, filtered, and concentrated to afford 33.7 g of 7-bromo-4-chloro-3-nitroquinoline as a beige solid. 1H NMR (300 MHz, CDC13) 8 9.26 (s, 1H), 8.41 (d, J= 1.8 Hz, 1H), 8.30 (d, J= 9. 0 HZ, 1H), 7.90 (dd, J = 8. 9,2. 1 HZ, 1H).
With trichlorophosphate; at 102℃; for 0.75h; Part D 7-Bromo-3-nitroquinolin-4-ol (42 g, 156 millimoles (mmol) ) was suspended in POC13 (130 mL) and brought to 102C under an atmosphere of N2. After 45 min, all of the solids had dissolved, so the reaction was cooled to room temperature (RT). The resulting solids were collected by filtration, washed with H20, and then partitioned with CH2C12 (3 L) and 2M Na2C03 (500 mL). The organic layer was separated, washed with H20 (1x), dried over Na2S04, filtered, and concentrated to afford 33.7 g of 7-bromo-4-chloro-3- nitroquinoline as a beige solid.
D7-Bromo-3-nitroquinolin-4-ol (42 g, 156 mmol) was suspended in POC13 (130 mL) and brought to 102 C under an atmosphere of N2. After 45 min, all of the solids had dissolved, so the reaction was cooled to room temperature. The resulting solids were collected by filtration, washed withH20, and then partitioned withCHzClz (3 L) and 2MNa2CO3 (500 mL). The organic layer was separated, washed withH20(lx), dried overNa2S04, filtered, and concentrated under reduced pressure to afford 33.7 g of 7-bromo-4-chloro-3-nitroquinoline as a beige solid. 'H NMR (300 MHz, CDC13) 8 9.26 (s, 1H), 8.41 (d, J= 1. 8 Hz, 1H), 8. 30 (d, J= 9.0 Hz, 1H), 7.90 (dd, J= 8.9, 2.1 Hz, 1H).
With trichlorophosphate; at 102℃; for 0.75h; Part D 7-Bromo-3-nitroquinolin-4-ol (42 g, 156 mmol) was suspended in POC13 (130 mL) and brought to 102 C under an atmosphere of N2. After 45 min, all of the solids had dissolved, so the reaction was cooled to room temperature. The resulting solids were collected by filtration, washed with H20, and then partitioned with CH2C12 (3 L) and 2M Na2C03 (500 mL). The organic layer was separated, washed with H2O (lx), dried over Na2S04, filtered, and concentrated under reduced pressure to afford 33.7 g of 7-bromo-4- chloro-3-nitroquinoline as a beige solid. 'H NMR (300 MHz, CDC13) 8 9.26 (s, 1H), 8. 41 (d, J= 1. 8 Hz, 1H), 8. 30 (d, J= 9.0 Hz, 1H), 7.90 (dd, J= 8.9, 2.1 Hz, 1H).
With trichlorophosphate; at 102℃; for 0.75h; Part D 7-Bromo-3-nitroquinolin-4-ol (42 g, 156 mmol) was suspended in POC13 (130 mL) and brought to 102 C under an atmosphere of N2. After 45 min, all of the solids had dissolved, so the reaction was cooled to room temperature. The resulting solids were collected by filtration, washed with H2O, and then partitioned with CHZCLZ (3 L) and 2M Na2C03 (500 mL). The organic layer was separated, washed with H20 (LX), dried over NA2S04, filtered, and concentrated to afford 33.7 g of 7- BROMO-4-CHLORO-3-NITROQUINOLINE as a beige solid.
With N-ethyl-N,N-diisopropylamine; trichlorophosphate; at 15 - 100℃; for 16h; General procedure: To a mixture of 6-bromo-3-nitro-quinoline-2,4-diol (30 g, 105.24 mmol, 1 eq) in POCh (484.12 g, 3.16 mol, 293.41 mL, 30 eq) was added N,N-diisopropylethylamine (40.81 g, 315.73 mmol, 55.00 mL, 3 eq) slowly at l 5C. The mixture was stirred at 100 C for 16 hrs. The mixture was concentrated in vacuum. The residue was poured into ice water (2000 mL), filtered and washed with H2O (500 mL x 3), and dried to provide 6-bromo-2,4-dichloro-3- nitro-quinoline (30 g, 93.18 mmol, 88.54% yield) as a yellow solid.

  • 10
  • [ 723280-98-6 ]
  • [ 870-46-2 ]
  • [ 749922-25-6 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; at 0 - 20℃; for 15h; Part A A suspension of <strong>[723280-98-6]7-bromo-4-chloro-3-nitroquinoline</strong> (75.00 g, 260.9 mmol) in 350 ML of dichloromethane was cooled to 0 C. under an atmosphere of nitrogen.The suspension was treated with triethylamine (43.25 ML, 326.1 mmol), which dissolved most of the material.A solution of tert-butyl carbazate (37.93 g, 287.0 mmol) in 250 ML of dichloromethane was added to the reaction mixture over 20 min.The reaction was allowed to slowly come to ambient temperature.After 15 h, the reaction mixture was washed with 5% Na2CO3 solution (2*100 ML) and water (100 ML).The combined aqueous washes were back-extracted with CHCl3 (50 ML).The combined organic portions were washed with brine (100 ML), dried over Na2SO4, filtered and concentrated under reduced pressure to yield 99.98 g of N'-(7-bromo-3-nitroquinolin-4-yl)hydrazine tert-butyl carboxylate as a dark red solid.
With triethylamine; In dichloromethane; at 0 - 20℃; for 15.3333h; Part A; A suspension of <strong>[723280-98-6]7-bromo-4-chloro-3-nitroquinoline</strong> (75.00 g, 260.9 mmol) in 350 mL of dichloromethane was cooled to 0 C under an atmosphere of nitrogen. The suspension was treated with triethylamine (43.25 mL, 326.1 mmol), which dissolved most of the material. A solution of tert-butyl carbazate (37.93 g, 287.0 mmol) in 250 mL of dichloromethane was added to the reaction mixture over 20 min. The reaction was allowed to slowly come to ambient temperature. After 15 h, the reaction mixture was washed with 5% Na2CO3 solution (2 X 100 mL) and water (100 mL). The combined aqueous washes were back-extracted with CHCl3 (50 mL). The combined organic portions were washed with brine (100 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to yield 99.98 g of tert-butyl N'-(7-bromo-3-nitroquinolm-4- yl)hydrazinecarboxylate as a dark red solid.
  • 11
  • [ 723280-98-6 ]
  • [ 2749-11-3 ]
  • [ 898819-03-9 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In N,N-dimethyl-formamide; at 20℃; Example 60; (11^-3-BrOmO-I l-methyl-10,1 l-dihydro-8H-[l,4]oxazino[4',3':l,2]imidazo[4,5- c] quinolin-6-amine; Part A; A 2-L, three-necked, Morton flask, equipped with overhead stirrer, was charged with <strong>[723280-98-6]7-bromo-4-chloro-3-nitroquinoline</strong> (28.75 g, 100 mmol), anhydrous DMF (200 mL) and triethylamine (28 mL, 200 mmol). The reaction mixture was stirred at ambient temperature and a solution of L-alaninol (7.51 g, 0.1 mol) in 100 mL of DMF was slowly added. After stirring overnight, the reaction mixture was treated with saturated aqueous K2CO3 solution (100 ml) and H2O (800 mL). The mixture was stirred vigorously for 2 hours to produce a yellow precipitate. The yellow solid was collected by vacuum filtration and dried with suction to give 30.9 g of (2S)-2-[7-bromo-3-nitroquinolin-4- yl)amino]propan-l-ol as bright-yellow crystals.
  • 12
  • [ 723280-98-6 ]
  • [ 103883-30-3 ]
  • [ 723284-02-4 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; Part A; To a solution of <strong>[723280-98-6]7-bromo-4-chloro-3-nitroquinoline</strong> (22.00 g, 76.52 mmol) indichloromethane (250 mL) was added triethylamine (16.0 mL, 115 mmol) followed by thedropwise addition of a solution of 4/?-(-)-(2,2-dimethyl)-l,3-dioxolane-4-methananiine(1 1 .04 g, 84.16 mmol) in dichloromethane (200 mL). The reaction was monitored byTLC, and after the starting material was consumed, the reaction mixture was transferred toa separatory funnel and washed with water (200 mL) and brine (200 mL), dried overNa2SC>4, filtered, and concentrated. The resulting yellow residue was triturated with water(200 mL) and the solid was collected by filtration and dried. The solid was sonicated indiethyl ether (100 mL) and isolated by filtration. The solid was dried under vacuum at 40°C to yield 7-bromo-A^-[(4JR)-2,2-dimethyl-l,3-dioxolan-4-yl]methyl}-3-nitroquinolin-4-amine (25.84 g) as a yellow solid, mp 136-137 °C.
  • 13
  • [ 723280-98-6 ]
  • [ 64930-17-2 ]
  • [ 723281-42-3 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloomethane; for 2h; To a suspension of <strong>[723280-98-6]7-bromo-4-chloro-3-nitroquinoline</strong> (U.S. Patent Application Publication No. US 2004/0147543 Example 1, 54.2 g, 0.19 mol) in dichloromethane (1 L) was added triethylamine (100 mL, 0.72 mol., 3.8 eq) in one portion. To the resulting solution was slowly added hydroxyisobutylamine (18.44 g, 0.21 mol, 1.1 eq). The reaction was complete within two hours. The reaction mixture was concentrated to dryness, and the residue was slurried in a solution of 1% aqueous sodium carbonate (600 mL) for two hours. The resulting bright yellow solid was collected by vacuum filtration and dried on the filter funnel overnight to provide 57 g of l-(7-bromo-3-nitroquinolin-4- ylamino)-2-methylpropan-2-ol.
  • 14
  • [ 723280-98-6 ]
  • [ 2906-12-9 ]
  • [ 872173-31-4 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In dichloromethane; for 48h; 7-Bromo-4-chloro-3-nitroquinoline (40 g) was dissolved in dichloromethane (1.4L) and triethylamine (23.3 mL). 3-Isopropoxypropylamine (19.3 mL) was added dropwise. After 48 hours, the reaction mixture was washed successively with water and saturated aqueous sodium chloride. The organic fraction was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. (7-Bromo-3- nitroquinolin-4-yl)-(3-isopropoxypropyl)amine was isolated as a tan solid (51.2g).
With triethylamine; In dichloromethane; for 48h; Part A 7-Bromo-4-chloro-3-nitroquinoline (40 g) was dissolved in dichloromethane (1.4 L) and triethylamine (23.3 mL). 3-Isopropoxypropylamine (19.3 mL) was added dropwise. After 48 hours, the reaction mixture was washed successively with water and saturated aqueous sodium chloride. The organic fraction was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. (7-Bromo-3- nitroquinolin-4-yl)- (3-isopropoxypropyl)amine was isolated as a tan solid (51.2g).
  • 15
  • [ 130290-79-8 ]
  • [ 723280-98-6 ]
  • [ 723283-83-8 ]
YieldReaction ConditionsOperation in experiment
Triethylamine (43 mL, 0.31 mol) was added in a single portion to a chilled (ice bath) suspension of <strong>[723280-98-6]7-bromo-4-chloro-3-nitroquinoline</strong> (60 g, (0.21 mol) in DMF (200 mL) to provide a solution. A solution of 1 -tetrahydro-2H-pytauan-4-ylmethylamine (36 g, 0.31 mole) in DMF (50 mL) was added dropwise. The reaction mixture was stirred at ambient temperature for 1 hour. The reaction mixture was chilled in an ice bath, then quenched with water (150 mL), and then stirred for 30 minutes. A solid was isolated by filtration, washed sequentially with water and diethyl ether, and then dried at 65 0C in a vacuum oven to provide 36.2 g of (7-bromo-3-nitroquinolin-4-yl)(tetrahydro-2H-pyran-4- ylmethyl)amine as a yellow solid.
  • 16
  • [ 723280-98-6 ]
  • [ 100-46-9 ]
  • [ 879004-36-1 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In N,N-dimethyl-formamide; at 20℃; for 72h; Triethylamine (5.24 g, 51.8 mmol) and benzylamine (4.15 mL, 38.0 mmol) were sequentially added to a solution of <strong>[723280-98-6]7-bromo-4-chloro-3-nitroquinoline</strong> (10.0 g, 34.5 mmol, see U.S. Patent Publication Application No. US 2004/0147543 (Hays et al.), Example 1 Parts A through D) in DMF (100 mL). The reaction was stirred at room temperature for three days, poured into water (800 mL), and stirred vigorously for 20 minutes. A precipitate formed and was isolated by filtration, washed with diethyl ether (800 mL), and dried under vacuum for four hours to provide 10.98 g of N-benzyl-7-bromo-3- nitroquinolin-4-amine as a yellow solid.
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