Methylamine → 6-Bromo-N-methylnicotinamide

Participants

Reaction Steps

N,N′-Carbonyldiimidazole (480 mg, 2.96 mmol) was added to a solution of 6-bromonicotinic acid (480 mg, 2.96 mmol) in dimethylsulfoxide (2 mL) and the mixture was stirred for 24 hours. Methylamine (2M in THF, 6 mL, 12 mmol) was then added and the mixture was stirred for a further 18 hours. The reaction mixture was evaporated under reduced pressure and the residue was diluted with water (25 mL) and extracted with dichloromethane (3×10 mL). The combined organic extracts were dried over sodium sulphate and concentrated in vacuo. The residue was purified by column chromatography on silica gel, eluting with ethyl acetate to afford the title compound as a colourless solid in 59% yield, 300 mg.

Provenance & Evidence