Thionyl Chloride → 6-Chloronicotinoyl Chloride

Participants

Reaction Steps

6-Chloronicotinic acid (67 g) was treated with thionyl chloride (130 ml) and the resulting mixture heated under reflux for 2 hours. After evaporation to dryness, 60°-80° petroleum ether (60 ml) was added, and the solution again evaporated to dryness. The resulting residue was taken up in petroleum ether (60°-80°) and the solution filtered. Partial evaporation of the filtrate, followed by cooling, gave the desired product, 6-chloronicotinoyl chloride, as a white precipitate, m.p. 45°-47° (73). The product was characterized by infra-red spectroscopy, and was used directly in the next stage without further purification.

Provenance & Evidence