Dimethylformamide → 5-Bromonicotinamide

Participants

Reaction Steps

Oxalyl chloride (1.33 ml) and N,N-dimethylformamide (catalytic amounts) were added dropwise under ice-cooling to a solution of 5-bromopyridine-3-carboxylic acid (2.02 g) in dichloromethane, and stirred for an hour. The solvent was evaporated in a evaporator, the residue was dissolved in tetrahydrofuran (10 ml), to which ammonia water (28%; 1 ml) was added dropwise under ice-cooling, and stirred at room temperature for 0.5 hours. After completion of the reaction, water was added to the reaction mixture and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and concentrated. The residue was purified with column chromatography to give 5-bromopyridine-3-carboxamide (734 mg).

Provenance & Evidence