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[ CAS No. 22246-66-8 ] {[proInfo.proName]}

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Chemical Structure| 22246-66-8
Chemical Structure| 22246-66-8
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Quality Control of [ 22246-66-8 ]

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Product Details of [ 22246-66-8 ]

CAS No. :22246-66-8 MDL No. :MFCD08437636
Formula : C9H9NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :VVXUPZRABQQCKL-UHFFFAOYSA-N
M.W : 163.17 Pubchem ID :22064719
Synonyms :

Calculated chemistry of [ 22246-66-8 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 47.89
TPSA : 38.33 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.77 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.67
Log Po/w (XLOGP3) : 0.74
Log Po/w (WLOGP) : 0.41
Log Po/w (MLOGP) : 0.84
Log Po/w (SILICOS-IT) : 1.82
Consensus Log Po/w : 1.1

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -1.62
Solubility : 3.9 mg/ml ; 0.0239 mol/l
Class : Very soluble
Log S (Ali) : -1.12
Solubility : 12.3 mg/ml ; 0.0752 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.01
Solubility : 0.161 mg/ml ; 0.000984 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.28

Safety of [ 22246-66-8 ]

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

Application In Synthesis of [ 22246-66-8 ]

* 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 [ 22246-66-8 ]

[ 22246-66-8 ] Synthesis Path-Downstream   1~15

  • 1
  • [ 368-39-8 ]
  • [ 22246-66-8 ]
  • [ 110568-76-8 ]
  • 2
  • [ 50727-04-3 ]
  • [ 22246-66-8 ]
  • 3
  • [ 22246-66-8 ]
  • [ 252061-66-8 ]
YieldReaction ConditionsOperation in experiment
79% 5-Hydroxy-2,3-dihydro-isoindol-1-oneTo a suspension of 5-Methoxy-2,3-dihydro-isoindol-1-one (5.65 g, 34.6 mmol) in dichloromethane (300 mL) was added boron tribromide (25.1 g, 100 mmol, 1.0 M solution in DCM) slowly over 20 min at 0 0C. The reaction was allowed to warm to room temperature after addition (3 h). The reaction was quenched with methanol (100 mL) at 0 0C and then allowed to stir for 3 h. The solution was concentrated and 500 mL of water was added and heated to 60 0C for 1 hour. The mixture was cooled and 5-Hydroxy-2,3-dihydro-isoindol-1-one was filtered off as a solid (4.10 g, 79%, CASNo. 252061-66-8). MS: ES: M+1: 150.0 (149.0)
72% A mixture Of 5-METHOXY-2, 3-DIHYDRO-ISOINDOL-1-ONE (3.7 g, 23 mmol) and boron tri- bromide (1 M in [CH2C12,] 15.2 mL, 88 mmol) in [CH2CI2] (30 mL) [AT-78 C] was stirred for 16 h at RT. The mixture was then cooled [TO-78 C] and [MEOH] (25 mL) was added. After lh at-78 C the mixture was evaporated and the residue purified by chromatography [(SI02,] [CH2C12] : 2N NH3-MeOH 98: 2 to 90: 10) to afford the title product (2.5 g, 72%) as an off- white solid. MS m/e = 148.0 (M-H+).
  • 4
  • [ 1007629-19-7 ]
  • [ 22246-66-8 ]
YieldReaction ConditionsOperation in experiment
With sodium hydroxide; water;pH 9.0;Product distribution / selectivity; The 2-Aminomethyl-5-methoxy-benzoic acid methyl ester hydrochloride (160 g, 0.69 moles) was dissolved in 4 L of water and the pH was adjusted to 9 using 1 M aqueous NaOH.At pH = 9, a white solid precipitated out of the clear solution. The solid was filtered and washed with water (500 mL). The solid 6-Methoxy-2,3-dihydro-isoindol-1-one was dried under vacuum at 40 0C for 48 h. (90 g, 80% over 2 steps).
  • 5
  • [ 127510-95-6 ]
  • [ 22246-66-8 ]
YieldReaction ConditionsOperation in experiment
84% With hydrogen;sponge nickel; In methanol; at 85℃; under 258.58099999999996 Torr;Product distribution / selectivity; Alternatively, to a pressure vessel was charged Sponge Nickel (511 mmoles; 30.0 g), 2-Cyano-5-methoxy-benzoic acid methyl ester (523 mmoles; 100 g) and Methanol (2.4 L). The mixture was purged with nitrogen and hydrogen and then hydrogenated at 85 0C under 50 psi hydrogen until the reaction was complete. The mixture was filtered, washed with 1 :1 methanol-dichloromethane, and concentrated to afford 84.0 g of the crude product. The crude product was triturated with 800 mL of 1 :1 ethyl acetate-isooctane at 60 0C and cooled <n="29"/>to rt. The white precipitate was filtered on a Whatmann filter and washed with cold 1:1 EtOAc-isooctane to afford 6-Methoxy-2,3-dihydro-isoindol-1-one (71 g, 84% yield).
  • 6
  • C13H17NO2 [ No CAS ]
  • [ 22246-66-8 ]
YieldReaction ConditionsOperation in experiment
74% With trifluoroacetic acid; for 2.5h;Reflux; General procedure: The corresponding N-tert-butylisoindolin-1-one was dissolved in neat trifluoroacetic acid and refluxed until the starting material was consumed indicated by TLC. The trifluoroacetic acid was then removed under reduced pressure and the residue was purified by column chromatography (hexanes/AcOEt).
  • 7
  • [ 85-44-9 ]
  • NaCl [ No CAS ]
  • [ 22246-66-8 ]
  • 8
  • [ 28281-76-7 ]
  • [ 22246-66-8 ]
  • 9
  • [ 610-35-5 ]
  • [ 22246-66-8 ]
  • 10
  • [ 134-08-7 ]
  • [ 22246-66-8 ]
  • 11
  • [ 1885-13-8 ]
  • [ 22246-66-8 ]
  • 12
  • [ 22246-66-8 ]
  • [ 659737-57-2 ]
YieldReaction ConditionsOperation in experiment
100% A mixture [OF 6-METHOXY-2, 3-DIHYDRO-ISOINDOL-1-ONE] (167 mg, 1.0 mmol) and boron tri- bromide (1 M in [CH2C12,] 3.6 mL, 3.6 mmol) in [CH2CI2] (8 mL) [AT-78C] was stirred for 18 h at RT. The mixture was then cooled to-78C and [MEOH] (20 mL) was added. After 2 h at-78C the mixture was evaporated and the residue purified by chromatography [(SI02,] [CH2CL2] : 2N NH3-MeOH 9: 1) to afford the title product (147 mg, 100%) as a white solid. MS m/e = 148.0 (M-H+).
95% 6-Hydroxy-2,3-dihydro-isoindol-1-one<strong>[22246-66-8]6-Methoxy-2,3-dihydro-isoindol-1-one</strong> (90 g, 0.55 moles, 1 equiv) was suspended in 2.52 L of DCM and 661 mL of BBr3 ( 0.66 moles, 1.2 equiv, 1.0 M solution in DCM) was added over 2 h at 0 0C. After the addition was complete, the reaction mixture was allowed to warm to room temperature over 3 h then stirred overnight. The reaction mixture was quenched by the addition of 1 L of MeOH at 0 0C and then stirred at room temperature for 3 h.Solvent was evaporated under vacuum, and the crude material was triturated with minimum amount of MeOH (-400 mL). The solid was filtered and dried under vacuum at 50 0C for 24 h to give 46.3 g of 6-Hydroxy-2,3-dihydro-isoindol-1-one with >98 % purity (56%). The mother liquor was concentrated and triturated with minimum amount of MeOH to afford 32 g of additional 6-Hydroxy-2,3-dihydro-isoindol-1-one with >90 % purity (39%).
79% With methanesulfonic acid; DL-methionine; at 85℃; for 24h;Product distribution / selectivity; Alternatively, to a flask containing <strong>[22246-66-8]6-Methoxy-2,3-dihydro-isoindol-1-one</strong> (435 mmol, 71.0 g) and methionine (771 mmol, 115 g) was added methanesulfonic acid (9.15 mol, 600 mL, 880 g). The reaction was stirred at 85 0C for 24 h and then was cooled and 1 L of water was slowly added to the mixture which caused an exotherm. The mixture was cooled to 5 0C. A tan solid was recovered via filtration, washed with water containing 1% HCI, water, and then dried- in vacuum oven at 45 0C overnight to afford 6-Hydroxy-2,3-dihydro-isoindol-1-one (51.4 g, 79%). MS: ES: M+1: 164.0 (163.1 ) 1H NMR (400 MHz, DMSO-d6) delta ppm 3.76 (s, 3 H) 4.23 (S, 2 H) 7.07-7.12 (m, 2H) 7.41 (d, J=8.97 Hz, 1 H) 8.47 (s, 1 H)
78% To a suspension of (74) (7.07 g, 43.4 mmol) in CH2Cl2 (600 ml) was added BBr3(IM in CH2Cl2, 86.7 ml). The reaction mixture was stirred at room temperature for 4 hr. The solvent and boron residue was removed in vacuo and the remaining solid was dissolved in CH2Cl2, the solution was neutralized with 1 N NaOH (PH = 6.5). Desired compound was precipitated out and filtered. The organic solution was separated and washed with sat. NaCl, dried over Na2SO4 to give the title compound (combined weight 5.1 g, 78 %). MS (ES) m/z 150.1.
With boron tribromide; In dichloromethane; at -78 - 20℃;Heating / reflux; Scheme 9Intermediate 23:Example Compound 13 (150 mg, 0.92 mmol) was dissolved in DCM (20 mL) and cooled to -78 C. To this mixture, BBr3 (1 M, 1.2 mL) was added dropwise. <n="76"/>After 1 hour, the mixture was warmed to room temperature and stirred for another 2 hours. Then, another portion of BBr3 (1 M, 1.2 ml_) was added and the resulting mixture was heated to reflux and stirred overnight. After cooling to room temperature, EtOAc (100 ml_) was added and the organics washed with water, brine and dried over Na2SO4. After concentration, the residue was used in the next step without further purification. HPLC-MS tR = 0.58 min (UV254 nm); mass calculated for formula C8H7NO2 149.0, observed LCMS m/z 150.1 (M+H).

  • 13
  • [ 286434-74-0 ]
  • [ 22246-66-8 ]
YieldReaction ConditionsOperation in experiment
43% With ammonium cerium(IV) nitrate; water; In acetonitrile; at 20℃; for 1h; A mixture [OF 6-METHOXY-2- (4-METHOXY-BENZYL)-2, 3-DIHYDRO-ISOINDOL-1-ONE] (300 mg, 1.1 mmol) and ammonium ceric nitrate (2.2 g, 4.0 mmol) in acetonitrile: water (12 mL, 2: 1) was stirred at RT for 1 h. Then the mixture was poured into water and extracted with ethyl acetate. The combined extracts were then washed with sodium hydrogen carbonate and water. The organic layer was then dried over sodium sulphate, filtered and evaporated. The residue was then purified by chromatography [(SI02,] dichloromethane: [MEOH] 20: 1) to afford the title product (75 mg, 43%) as a light yellow solid. MS m/e = 164.2 (M). Alternatively, a mixture [OF 6-METHOXY-2- (4-METHOXY-BENZYL)-2, 3-DIHYDRO-ISOINDOL-1-ONE] (98.5 mg, 0.35 mmol) in dichlormethane (10 mL) containing TFA (1.6 mL, 20.8 mmol) and TfOH (0.6 mL, 7.0 mmol) was heated overnight at [40 C.] Then the mixture was poured into sodium hydrogen carbonate and water and the product extracted with di- chloromethane. The combined organic layers were then dried over sodium sulphate, filtered and evaporated. The residue was then purified by chromatography [(SI02,] dichloro- methane: [MEOH] 20: 1) to afford the title product (24 mg, 42%) as a light yellow solid. MS m/e = 164.2 (M). i) 6-Hydroxy-2, [3-DIHYDRO-ISOINDOL-1-ONE] A mixture [OF 6-METHOXY-2, 3-DIHYDRO-ISOINDOL-1-ONE] (167 mg, 1.0 mmol) and boron tri- bromide (1 M in [CH2C12,] 3.6 mL, 3.6 mmol) in [CH2CI2] (8 mL) [AT-78C] was stirred for 18 h at RT. The mixture was then cooled to-78C and [MEOH] (20 mL) was added. After 2 h at-78C the mixture was evaporated and the residue purified by chromatography [(SI02,] [CH2CL2] : 2N NH3-MeOH 9: 1) to afford the title product (147 mg, 100%) as a white solid. MS m/e = 148.0 (M-H+).
42% With trifluorormethanesulfonic acid; trifluoroacetic acid; In dichloromethane; at 40℃; A mixture [OF 6-METHOXY-2- (4-METHOXY-BENZYL)-2, 3-DIHYDRO-ISOINDOL-1-ONE] (300 mg, 1.1 mmol) and ammonium ceric nitrate (2.2 g, 4.0 mmol) in acetonitrile: water (12 mL, 2: 1) was stirred at RT for 1 h. Then the mixture was poured into water and extracted with ethyl acetate. The combined extracts were then washed with sodium hydrogen carbonate and water. The organic layer was then dried over sodium sulphate, filtered and evaporated. The residue was then purified by chromatography [(SI02,] dichloromethane: [MEOH] 20: 1) to afford the title product (75 mg, 43%) as a light yellow solid. MS m/e = 164.2 (M). Alternatively, a mixture [OF 6-METHOXY-2- (4-METHOXY-BENZYL)-2, 3-DIHYDRO-ISOINDOL-1-ONE] (98.5 mg, 0.35 mmol) in dichlormethane (10 mL) containing TFA (1.6 mL, 20.8 mmol) and TfOH (0.6 mL, 7.0 mmol) was heated overnight at [40 C.] Then the mixture was poured into sodium hydrogen carbonate and water and the product extracted with di- chloromethane. The combined organic layers were then dried over sodium sulphate, filtered and evaporated. The residue was then purified by chromatography [(SI02,] dichloro- methane: [MEOH] 20: 1) to afford the title product (24 mg, 42%) as a light yellow solid. MS m/e = 164.2 (M). i) 6-Hydroxy-2, [3-DIHYDRO-ISOINDOL-1-ONE] A mixture [OF 6-METHOXY-2, 3-DIHYDRO-ISOINDOL-1-ONE] (167 mg, 1.0 mmol) and boron tri- bromide (1 M in [CH2C12,] 3.6 mL, 3.6 mmol) in [CH2CI2] (8 mL) [AT-78C] was stirred for 18 h at RT. The mixture was then cooled to-78C and [MEOH] (20 mL) was added. After 2 h at-78C the mixture was evaporated and the residue purified by chromatography [(SI02,] [CH2CL2] : 2N NH3-MeOH 9: 1) to afford the title product (147 mg, 100%) as a white solid. MS m/e = 148.0 (M-H+).
  • 14
  • [ 788081-99-2 ]
  • [ 22246-66-8 ]
YieldReaction ConditionsOperation in experiment
86% With ammonia; In methanol; at 125℃; for 2h; A solution of methyl 2-(bromomethyl)-5-methoxybenzoate ((75), 5.0 g, 19.3 mmol) in MeOH was placed in pressure flask and to it ammonia/methanol (2M, 30 ml) was added. Resulting mixture was stirred at 125 0C for 2 hr. The solvent and excess NH3 was removed in vacuo and the residue was triturated with Hexane/EtOAc (1:2 ratio). The compound was filtrated under vacuum and air-dried for 2 hr to give the title compound ( 2.51 g, 65 % ) as a pale yellow solid. The filtrated was concentrated and purified on silica gel (Hexane/EtOAc/MeOH 3:1:0.5 ratio) to yield another 270 mg of desired compound. Combined yield was 86 %. MS (ES) m/z 164.1.
67% With ammonia; In methanol; at 60℃; Intermediate 13 :Compound 12 (32.0 g, 124.0 mmol) was dissolved in 7 M ammonia in MeOH (150 ml_) and stirred in a sealed pressure flask at 60 C overnight. The reaction mixture was cooled and the solvent was removed under reduced pressure. The residue was suspended in ethyl acetate and stirred for 30 minutes. The solids were filtered and dissolved in methylene chloride. The methylene chloride was washed with water, dried over sodium sulfate, and concentrated to provide the desired product 13 (13.5 g, 67%). Mass calculated for formula C9H9 NO2, 163.17, observed LCMS m/z 164.2 (M+H), NMR (H1); 4.20(2H,CH2) 3.73(3H, -OCH3),3.88,6.86-7.5(m,3H,Aromatic), 8.0(NH)
67% With ammonia; In methanol; at 60℃;Sealed flask; Part C: Compound 3 (32.0 g, 124.0 mmol) was dissolved in 7 M ammonia in MeOH (150 mL) and stirred in a sealed pressure flask at 60 0C overnight. The reaction mixture was cooled and the solvent was removed under reduced pressure. The residue was suspended in ethyl acetate and stirred for 30 minutes. The solids were filtered and dissolved in methylene chloride. The methylene chloride solution was washed with water, dried over sodium sulfate, and concentrated to provide the desired product 4 (13.5 g, 67%).
67% With ammonia; In methanol; at 60℃; Part C: Compound 302 (32.0 g, 124.0 mmol) was dissolved in 7 M ammonia in MeOH (150 ml) and stirred in a sealed pressure flask at 60 0C overnight. The reaction mixture was cooled and the solvent was removed under reduced pressure. The residue was suspended in ethyl acetate and stirred for 30 minutes. The solids were filtered and dissolved in methylene chloride. The methylene chloride was washed with water, dried over sodium sulfate, and concentrated to provide the desired product 303 (13.5 g, 67%).
67% With ammonia; In methanol; at 60℃;Sealed tube; Compound 3 (32.0 g, 124.0 mmol) was dissolved in 7 M ammonia in MeOH (150 mL) and stirred in a sealedpressure flask at 60 C overnight. The reaction mixture was cooled and the solvent was removed under reduced pressure.The residue was suspended in ethyl acetate and stirred for 30 minutes. The solids were filtered and dissolved in methylenechloride. The organic layer was washed with water, dried over sodium sulfate, and concentrated to provide the desiredproduct 4 (13.5 g, 67%).

  • 15
  • [ 100367-77-9 ]
  • [ 22246-66-8 ]
  • [ 1023298-62-5 ]
YieldReaction ConditionsOperation in experiment
91% With potassium phosphate;tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 105℃; for 12h; Example 39; Preparation of Intermediate Compound 39A; To a pressure tube charged with 2-bromo-4-carboethoxythiazole (2.5 g, 10.6 mmol) and a stir bar was added 6-methoxyisoindolin-1 -one (2.1 g, 12.7 mmol), K3PO4 (4.9 g, 23.3 mmol), Pd2(dba)3 (0.58 g, 0.64 mmol), Xant-Phos (0.62g, 1.1 mmol). Dioxane (20 mL) was added and N2 was bubbled thru the solution for 10 EPO <DP n="152"/>min before the vessel was capped. The mixture stirred at 105 C for 12h and was cooled to rt. The mixture was filtered thru a pad of Celite and was washed with CH2CI2/Me0H (20:1 ; 2 x 10 mL). The resulting filtrate was concentrated under reduced pressure and place under high vacuum. The crude product was purified using flash chromatography using a gradient from CH2Cb to 97:3 CH2CI2/acetone to provide 3.1 g (91% yield) of compound 39A as a brown solid. LC-MS [M+H] = 400.2; 98% purity.
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