2-methylisoindole-1,3-dione

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:250.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: An addition funnel is charged with 46 parts of phthalic anhydride. After the anhydride is melted, it is added as a slow stream through an adaptor heated at 250° C containing a side arm. The adaptor is connected to a glass tube filled with glass beads. Through the side arm of the adaptor there is introduced methylamine gas. The mixture of the methylamine gas and the liquid phthalic anhydride is allowed to flow into the glass tube heated at 300° C which contains glass beads. At the bottom of the glass tube there is a receiver in the form of 100 ml flask fitted with a side arm. The methylamine gas is introduced at a rate of 1-2 parts per minute. The addition of the molten phthalic anhydride is completed in about 10-15 minutes while excess methylamine and water produced in the reaction being vented through the side arm. There is obtained a 72% yield of N-methylphthalimide as a white solid having a melting point of 129.5°-132° C. No unreacted phthalic anhydride and less than 1% by weight of bis-(N-methyl)amide of phthalic anhydride was detected in the final product based on liquid chromotography. it is added as a slow stream through an adaptor containing a side arm The adaptor is connected to a glass tube filled with glass beads heated at 300° C which fitted with a side arm produced in the reaction

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: NaBH4 (566 mg, 14.91 mmol) was added to a stirring solution of 2-methyl-isoindole-1,3-dione (2.0 g, 12.42 mmol) in methanol (20 mL) at 0° C. Stirring at 0° C. was maintained for 1 hour, then the reaction was warmed to room temperature. Additional NaBH4 (566 mg, 14.91 mmol) was added in order to push the reaction to completion. The reaction was then quenched with acetic acid (5 mL) and partitioned between water and dichloromethane. The organic layer was washed several times with water and concentrated under vacuum to give 659-mg of the sub-title compound as a white solid. MS: ESI (positive): 164 (M+H). was maintained for 1 hour the reaction was warmed to room temperature the reaction to completion The reaction was then quenched with acetic acid (5 mL) partitioned between water and dichloromethane The organic layer was washed several times with water concentrated under vacuum

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: NaBH4 (566 mg, 14.91 mmol) was added to a stirring solution of 2-methyl-isoindole-1,3-dione (2.0 g, 12.42 mmol) in methanol (20 mL) at 0° C. Stirring at 0° C. was maintained for 1 hour, then the reaction was warmed to room temperature. Additional NaBH4 (566 mg, 14.91 mmol) was added in order to push the reaction to completion. The reaction was then quenched with acetic acid (5 mL) and partitioned between water and dichloromethane. The organic layer was washed several times with water and concentrated under vacuum to give 659-mg of the sub-title compound as a white solid. MS: ESI (positive): 164 (M+H). was maintained for 1 hour the reaction was warmed to room temperature the reaction to completion The reaction was then quenched with acetic acid (5 mL) partitioned between water and dichloromethane The organic layer was washed several times with water concentrated under vacuum

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: At 0° C., (4-methoxybenzyl)magnesium chloride (0.25 M in THF) (37 ml, 9.3 mmol) was added to 2-methylisoindoline-1,3-dione (1.00 g, 6.2 mmol) in THF (3.0 mL) (Reference: Synthetic Comm. 2004, 34(7), 1301-1308). The mixture was stirred at 0° C. for 5 minutes, then quenched with 10 mL of water. The reaction was warmed to RT and concentrated to yield 2-(2-(4-methoxyphenyl)acetyl)-N-methylbenzamide as a white solid (crude). The material was carried on to next step without further purification. MS m/z=284 [M+1]+. Calc'd for C17H17NO3: 283.33. quenched with 10 mL of water The reaction was warmed to RT concentrated

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: NaBH4 (566 mg, 14.91 mmol) was added to a stirring solution of 2-methyl-isoindole-1,3-dione (2.0 g, 12.42 mmol) in methanol (20 mL) at 0° C. Stirring at 0° C. was maintained for 1 hour, then the reaction was warmed to room temperature. Additional NaBH4 (566 mg, 14.91 mmol) was added in order to push the reaction to completion. The reaction was then quenched with acetic acid (5 mL) and partitioned between water and dichloromethane. The organic layer was washed several times with water and concentrated under vacuum to give 659 mg of the sub-title compound as a white solid. MS: ESI (positive): 164 (M+H). was maintained for 1 hour the reaction was warmed to room temperature the reaction to completion The reaction was then quenched with acetic acid (5 mL) partitioned between water and dichloromethane The organic layer was washed several times with water concentrated under vacuum

反応条件: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 3.4 g of potassium borohydride are added slowly to a suspension of 10 g of N-methylphthalimide in 220 cm3 of methanol under an inert atmosphere. The reaction mixture is stirred at a temperature in the region of 20° C. for 20 hours, followed by dropwise addition of 200 cm3 of distilled water. The solvent is then partially evaporated off (about 120 cm3) under reduced pressure (2 kPa) at a temperature in the region of 35° C., and the residue is diluted with 400 cm3 of distilled water. The mixture is extracted with 400 cm3 of ethyl acetate. The organic phase is dried over magnesium sulfate, filtered and then concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 30° C. 4.5 g of 3-hydroxy-2-methyl-2,3-dihydroisoindol-1-one are thus obtained in the form of a white powder melting at 130° C. The solvent is then partially evaporated off (about 120 cm3) under reduced pressure (2 kPa) at a temperature in the region of 35° C. the residue is diluted with 400 cm3 of distilled water The mixture is extracted with 400 cm3 of ethyl acetate The organic phase is dried over magnesium sulfate filtered concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 30° C

反応条件: temp:20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 3.4 g of potassium borohydride are added slowly to a suspension of 10 g of N-methylphthalimide in 220 cm3 of methanol under an inert atmosphere. The reaction mixture is stirred at a temperature in the region of 20° C. for 20 hours, followed by dropwise addition of 200 cm3 of distilled water. The solvent is then partially evaporated off (about 120 cm3) under reduced pressure (2 kPa) at a temperature in the region of 35° C., and the residue is diluted with 400 cm3 of distilled water. The mixture is extracted with 400 cm3 of ethyl acetate. The organic phase is dried over magnesium sulfate, filtered and then concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 30° C. 4.5 g of 3-hydroxy-2-methyl-2,3-dihydroisoindol-1-one are thus obtained in the form of a white powder melting at 130° C. The solvent is then partially evaporated off (about 120 cm3) under reduced pressure (2 kPa) at a temperature in the region of 35° C. the residue is diluted with 400 cm3 of distilled water The mixture is extracted with 400 cm3 of ethyl acetate The organic phase is dried over magnesium sulfate filtered concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 30° C

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: At 0° C., (4-methoxybenzyl)magnesium chloride (0.25 M in THF) (37 ml, 9.3 mmol) was added to 2-methylisoindoline-1,3-dione (1.00 g, 6.2 mmol) in THF (3.0 mL) (Reference: Synthetic Comm. 2004, 34(7), 1301-1308). The mixture was stirred at 0° C. for 5 minutes, then quenched with 10 mL of water. The reaction was warmed to RT and concentrated to yield 2-(2-(4-methoxyphenyl)acetyl)-N-methylbenzamide as a white solid (crude). The material was carried on to next step without further purification. MS m/z=284 [M+1]+. Calc'd for C17H17NO3: 283.33. quenched with 10 mL of water The reaction was warmed to RT concentrated