N-methyl-2-pyrrolidone → 1-Methyl-1H-indole-6-carbonitrile

Participants

Reaction Conditions

Reaction Steps

Cuprous cyanide (12.8 g, 143 mmol) was added to a stirred solution of 6-bromo-1-methylindole (10 g, 47 mmol) in N-methylpyrrolidinone (60 ml) under a nitrogen atmosphere. The reaction mixture was heated at 150° C. for 48 h. The reaction mixture was cooled and partitioned between ethyl acetate (200 ml) and aqueous ammonia (200 ml of 0.88M). The organic layer was washed with brine (3×200 ml). dried (MgSO4) and concentrated. Flash column chromatography (elution with 70% hexane/30% ethyl acetate) gave the product as a crystalline white solid (5.3 g).

Provenance & Evidence