Oxalyl chloride → 2-Chloronicotinoyl chloride

Participants

Reaction Conditions

Reaction Steps

To a suspension of 2-chloronicotinic acid (37.8 g, 0.240 mol) in dry DCM (150 mL) and DMF (0.1 mL) cooled in an ice-bath was added oxalyl chloride (22.9 mL, 0.264 mol) dropwise over a period of 15 min. After stirring for 1 h at 0° C., the reaction mixture was heated to reflux for 6 h (the mixture became a clear brownish solution). The solvent and the excess oxalyl chloride was evaporated under reduced pressure. Toluene (100 mL) was added to the residue and the mixture was evaporated. The obtaining residue was purified by vacuum distillation to give 2-chloronicotinoyl chloride (41.7 g, 99%); bp 98–100° C./2 mmHg, mp 38–39° C. (from Lancaster catalog). Caution: Distillation may need a special care due to the high melting point of the product.

Provenance & Evidence