Oxalyl chloride → 2-Chloronicotinoyl chloride

Participants

Reaction Steps

A mixture of 2-chloronicotinic acid (20 g, 0.127 mmol) and oxalyl chloride (13.3 mL, 0.152 mmol) in 2 drops of DMF and 200 mL of methylene chloride was stirred at room temperature for approximately 14 hours. The mixture was stirred at reflux temperature for 1 hour. The solution was cooled and partitioned between 100 mL of ice-cold aqueous sodium bicarbonate and 300 mL of methylene chloride. The organic layer was washed with brine, dried (Na2SO4) and concentrated to give 2-chloronicotinic acid chloride (8.8 g, 49.5 mmol).

Provenance & Evidence