Pyridine → 2-(7-Chloro-1,8-naphthyridin-2-yl)-3-dimethylaminocarbonyloxy-isoindolin-1-one

Participants

Reaction Steps

Pyridine (10 cc.), triethylamine (5 cc.) and dimethylcarbamoyl chloride (1.61 g.) are added successively to a suspension of 2-(7-chloro-1,8-naphthyridin-2-yl)-3-hydroxy-isoindolin-1-one (3.11 g.) in methylene chloride (50 cc.). The reaction mixture is stirred for 16 hours at a temperature of about 20° C. and water (50 cc.) and methylene chloride (25 cc.) are then added. The aqueous layer is decanted off and washed with methylene chloride (2 × 25 cc.). The organic layers are combined, washed with water (2 × 25 cc.), dried over sodium sulphate and evaporated to dryness under reduced pressure. Recrystallisation of the residue obtained from acetonitrile (45 cc.) gives 2-(7-chloro-1,8-naphthyridin-2-yl)-3-dimethylaminocarbonyloxy-isoindolin-1-one (2.8 g.) melting at 218° C.

Provenance & Evidence