Benzylamine → Methyl 2-benzylisoindoline-5-carboxylate

Participants

Reaction Steps

TEA was added at room temperature, in the course of 15 minutes, to a solution of methyl 3,4-bis(bromomethyl)benzoate (9.3 g; 1 equiv.) and benzylamine (4.3 g; 1.4 equiv.) in 83.7 ml of benzene. The resulting reaction mixture was first stirred for 30 minutes at room temperature and then heated for 20 hours at reflux (110-120° C.). When the conversion was complete, the reaction mixture was cooled to room temperature and filtered. The filtrate was taken up in 100 ml of dichloromethane and washed 2× with 5% sodium carbonate solution. The combined organic phases were dried over sodium sulfate and the solvent was removed under reduced pressure. Purification by column chromatography (silica gel, 5% ethyl acetate/hexane) yielded methyl 2-benzylisoindoline-5-carboxylate (2.2 g; 28.3%) in the form of a solid.

Provenance & Evidence