Acetic Acid → Phthalimide

Participants

Reaction Steps

To a solution of 2-(2-methylamino-ethyl)-isoindole-1,3-dione (1 eq) in dichloromethane was added nicotinaldehyde (1.5 eq), sodium acetoborohydride (4.5 eq) and acetic acid (1.5 eq). After stirring at room temperature for 1 h, NaHCO3 (sat.) was added to the reaction mixture followed by an extraction with dichloromethane. The organic phase was washed with H2O, NaCl (sat.) (50 ml), dried over sodium sulfate, filtered, and concentrated. The crude product was purified by flash chromatography using a solvent gradient of 97% DCM, 3% MeOH, and 0.1% TEA (2L) to yield 2-[2-methyl-pyridin-3-ylmethyl-amino)-ethyl]-isoindole-1,3-dione (57%). MH+(296)

Provenance & Evidence