7-氟-3,4-二氢-2H-2(1H)-喹喔啉酮

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 7-fluoro-3,4-dihydro-1H-quinoxalin-2-one (4.00 g, 24.1 mmol, 1.0 eq), sodium hydroxide (1.93 g, 48.2 mmol, 2.0 eq) and of 3% hydrogen peroxide solution (50 mL) is refluxed for 2 hours, then it is acidified by slow addition of acetic acid. The resulting mixture is cooled to room temperature, the precipitated solid is collected by filtration, washed with ice-water, and dried under vacuum to give a crude that is purified by column chromatography (silica gel, eluent: dichloromethane:methanol, 50:1, v/v) to afford 7-fluoro-quinoxalin-2-ol as a yellow solid (2.60 g, 69% yield). the precipitated solid is collected by filtration washed with ice-water dried under vacuum to give a crude that is purified by column chromatography (silica gel, eluent

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 7-fluoro-3,4-dihydro-1H-quinoxalin-2-one (4.00 g, 24.1 mmol, 1.0 eq), sodium hydroxide (1.93 g, 48.2 mmol, 2.0 eq) and of 3% hydrogen peroxide solution (50 mL) is refluxed for 2 hours, then it is acidified by slow addition of acetic acid. The resulting mixture is cooled to room temperature, the precipitated solid is collected by filtration, washed with ice-water, and dried under vacuum to give a crude that is purified by column chromatography (silica gel, eluent: dichloromethane:methanol, 50:1, v/v) to afford 7-fluoro-quinoxalin-2-ol as a yellow solid (2.60 g, 69% yield). the precipitated solid is collected by filtration washed with ice-water dried under vacuum to give a crude that is purified by column chromatography (silica gel, eluent

反应条件: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Iron powder (6.52 g, 116.8 mmol, 5.0 eq) is added at room temperature to a stirred solution of (4-fluoro-2-nitro-phenylamino)-acetic acid (6.85 g, 23.4 mmol, 1.0 eq) in glacial acetic acid (40 mL). The resulting suspension is heated at 90° C. for 3 hours, then cooled to room temperature, diluted with ethyl acetate (40 mL), and filtered through silica gel. The filtrate is concentrated to give a crude that is purified by column chromatography (silica gel, eluent: ethyl acetate:petroleum ether, 1:3, v/v) to afford 7-fluoro-3,4-dihydro-1H-quinoxalin-2-one as a brown solid (4.01 g, 72% yield). cooled to room temperature filtered through silica gel The filtrate is concentrated to give a crude that is purified by column chromatography (silica gel, eluent

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 7-fluoro-3,4-dihydro-2(1H)-quinoxalinone (15.65 g, 92.88 mmol) in dichloromethane/methanol (1:1, 600 mL) was stirred with manganese dioxide (78.25 g) at room temperature for 1.5 h. The mixture was filtered through kieselguhr, washing through several times with 10% methanol/dichloromethane (˜1 L), and the filtrate was evaporated to give the product (7.27 g). Extraction of the residual filtration solids several times with dimethylformamide at 60-70° C., followed by filtration and evaporation of the extracts, gave more product (6.66 g), the total yield being 13.93 g (91.5%). The mixture was filtered through kieselguhr washing through several times with 10% methanol/dichloromethane (˜1 L) the filtrate was evaporated

反应条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Methyl N-(4-fluoro-2-nitrophenyl)glycinate (40 g, 175 mmol) in water (2000 mL) was heated to 90° C. Sodium dithionite (243.8 g, 1401 mmol) was added in portions. The resulting mixture was heated at 100° C. for 2 h, then allowed to cool. The solid was filtered off, washed with water and dried to give the product (13.75, 47%). Concentration of the liquor by evaporation to ˜700 mL gave a further precipitate which was filtered off, washed and dried as before to give more product (1.90 g: total yield 15.65 g, 54%). to cool The solid was filtered off washed with water dried to give the product (13.75, 47%) Concentration of the liquor by evaporation to ˜700 mL gave a further precipitate which was filtered off washed dried as before to give more product (1.90 g: total yield 15.65 g, 54%)

反应条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Methyl N-(4-fluoro-2-nitrophenyl)glycinate (40 g, 175 mmol) in water (2000 mL) was heated to 90° C. Sodium dithionite (243.8 g, 1401 mmol) was added in portions. The resulting mixture was heated at 100° C. for 2 h, then allowed to cool. The solid was filtered off, washed with water and dried to give the product (13.75, 47%). Concentration of the liquor by evaporation to ˜700 mL gave a further precipitate which was filtered off, washed and dried as before to give more product (1.90 g: total yield 15.65 g, 54%). to cool The solid was filtered off washed with water dried to give the product (13.75, 47%) Concentration of the liquor by evaporation to ˜700 mL gave a further precipitate which was filtered off washed dried as before to give more product (1.90 g: total yield 15.65 g, 54%)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 7-fluoro-3,4-dihydro-1H-quinoxalin-2-one (4.00 g, 24.1 mmol, 1.0 eq), sodium hydroxide (1.93 g, 48.2 mmol, 2.0 eq) and of 3% hydrogen peroxide solution (50 mL) is refluxed for 2 hours, then it is acidified by slow addition of acetic acid. The resulting mixture is cooled to room temperature, the precipitated solid is collected by filtration, washed with ice-water, and dried under vacuum to give a crude that is purified by column chromatography (silica gel, eluent: dichloromethane:methanol, 50:1, v/v) to afford 7-fluoro-quinoxalin-2-ol as a yellow solid (2.60 g, 69% yield). the precipitated solid is collected by filtration washed with ice-water dried under vacuum to give a crude that is purified by column chromatography (silica gel, eluent

反应条件: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Iron powder (6.52 g, 116.8 mmol, 5.0 eq) is added at room temperature to a stirred solution of (4-fluoro-2-nitro-phenylamino)-acetic acid (6.85 g, 23.4 mmol, 1.0 eq) in glacial acetic acid (40 mL). The resulting suspension is heated at 90° C. for 3 hours, then cooled to room temperature, diluted with ethyl acetate (40 mL), and filtered through silica gel. The filtrate is concentrated to give a crude that is purified by column chromatography (silica gel, eluent: ethyl acetate:petroleum ether, 1:3, v/v) to afford 7-fluoro-3,4-dihydro-1H-quinoxalin-2-one as a brown solid (4.01 g, 72% yield). cooled to room temperature filtered through silica gel The filtrate is concentrated to give a crude that is purified by column chromatography (silica gel, eluent

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 7-fluoro-3,4-dihydro-1H-quinoxalin-2-one (4.00 g, 24.1 mmol, 1.0 eq), sodium hydroxide (1.93 g, 48.2 mmol, 2.0 eq) and of 3% hydrogen peroxide solution (50 mL) is refluxed for 2 hours, then it is acidified by slow addition of acetic acid. The resulting mixture is cooled to room temperature, the precipitated solid is collected by filtration, washed with ice-water, and dried under vacuum to give a crude that is purified by column chromatography (silica gel, eluent: dichloromethane:methanol, 50:1, v/v) to afford 7-fluoro-quinoxalin-2-ol as a yellow solid (2.60 g, 69% yield). the precipitated solid is collected by filtration washed with ice-water dried under vacuum to give a crude that is purified by column chromatography (silica gel, eluent

反应条件: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Iron powder (6.52 g, 116.8 mmol, 5.0 eq) is added at room temperature to a stirred solution of (4-fluoro-2-nitro-phenylamino)-acetic acid (6.85 g, 23.4 mmol, 1.0 eq) in glacial acetic acid (40 mL). The resulting suspension is heated at 90° C. for 3 hours, then cooled to room temperature, diluted with ethyl acetate (40 mL), and filtered through silica gel. The filtrate is concentrated to give a crude that is purified by column chromatography (silica gel, eluent: ethyl acetate:petroleum ether, 1:3, v/v) to afford 7-fluoro-3,4-dihydro-1H-quinoxalin-2-one as a brown solid (4.01 g, 72% yield). cooled to room temperature filtered through silica gel The filtrate is concentrated to give a crude that is purified by column chromatography (silica gel, eluent

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 7-fluoro-3,4-dihydro-1H-quinoxalin-2-one (4.00 g, 24.1 mmol, 1.0 eq), sodium hydroxide (1.93 g, 48.2 mmol, 2.0 eq) and of 3% hydrogen peroxide solution (50 mL) is refluxed for 2 hours, then it is acidified by slow addition of acetic acid. The resulting mixture is cooled to room temperature, the precipitated solid is collected by filtration, washed with ice-water, and dried under vacuum to give a crude that is purified by column chromatography (silica gel, eluent: dichloromethane:methanol, 50:1, v/v) to afford 7-fluoro-quinoxalin-2-ol as a yellow solid (2.60 g, 69% yield). the precipitated solid is collected by filtration washed with ice-water dried under vacuum to give a crude that is purified by column chromatography (silica gel, eluent

反应条件: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Iron powder (6.52 g, 116.8 mmol, 5.0 eq) is added at room temperature to a stirred solution of (4-fluoro-2-nitro-phenylamino)-acetic acid (6.85 g, 23.4 mmol, 1.0 eq) in glacial acetic acid (40 mL). The resulting suspension is heated at 90° C. for 3 hours, then cooled to room temperature, diluted with ethyl acetate (40 mL), and filtered through silica gel. The filtrate is concentrated to give a crude that is purified by column chromatography (silica gel, eluent: ethyl acetate:petroleum ether, 1:3, v/v) to afford 7-fluoro-3,4-dihydro-1H-quinoxalin-2-one as a brown solid (4.01 g, 72% yield). cooled to room temperature filtered through silica gel The filtrate is concentrated to give a crude that is purified by column chromatography (silica gel, eluent