Phthalimide → Ammonium Hydroxide

Participants

Reaction Steps

Cool a mixture of phthalimide (0.54 g, 3.7 mmol) and PPh3 (0.95 g, 3.6 mmol) in tetrahydrofuran (5.0 mL) to 0° C. Add a solution of 2-pyridine propanol (0.50 g, 3.7 mmol) and diethyl azodicarboxylate (0.60 mL, 3.8 mmol) in tetrahydrofuran (5.0 mL) dropwise over 4 minutes. After 4 hours, concentrate the reaction mixture, redissolve in diethyl ether (50 mL) and filter. Concentrate the filtrate. Perform flash chromatography on silica gel eluting with 20% of a 80:18:2 CHCl3/MeOH/concentrated NH4OH solution in methylene chloride to afford 2-(3-pyridin-2-yl-propyl)isoindole-1,3-dione as a red oil which is used without further purification.

Provenance & Evidence