Benzylamine → N-benzyl-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)acetamide

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Reaction Steps

To a stirred solution of N-phthaloylglycine (11.92 g, 58 mmol) in dichloromethane (200 mL) at room temperature, oxalyl chloride (7.5 mL, 87 mmol) was added. DMF (two drops) was then added. The resulting solution was concentrated after stirring four hours at room temperature. Dichloromethane (100 mL, dry) was then added to the residue. Benzylamine (9.5 mL, 87 mmol) was added slowly into the resulting solution. Triethylamine (12 mL, 87 mmol) was then added slowly into the solution. Dichloromethane (200 mL) and methanol (50 mL) were added 30 min after the completed addition of triethylamine. The resulting solution was extracted with 2 N HCl solution twice, 1 N NaOH solution one time and 1 N HCl one time, and then dried over MgSO4. The solution was filtered and concentrated to yield N-benzyl-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-acetamide as a white solid.

Provenance & Evidence