Dimethylformamide → 2,6-Dichloropyridine-3-carboxamide

Participants

Reaction Steps

A suspension of 2,6-dichloronicotinic acid (5 g, 26.0 mmol) in CH2Cl2 (20 mL) was treated with oxalyl dichloride (3.97 g, 31.3 mmol) and few drops of DMF, and stirred at rt. The generation of bubbles was observed and the reaction mixture gradually became clear. The resulting clear solution was concentrated on a rotary evaporator to remove traces of oxalyl chloride, dissolved in CH2Cl2 (20 mL), treated with aqueous NH4OH (3.47 mL, 52.1 mmol) added drop-wise, and stirred at rt for 1 h. The resulting mixture was diluted with CH2Cl2 (white precipitate doesn't all dissolve), washed with satd. NaHCO3, and concentrated to obtain 2.97 g of 2,6-dichloronicotinamide as a white solid. LCMS: (M+H)+=190.96 (100%) 192.93 (70%) 194.93 (20%).

Provenance & Evidence