Thionyl Chloride → 2-(Chloromethyl)-4-methoxypyridine hydrochloride

Participants

Reaction Steps

15 ml of thionyl chloride are added dropwise to a solution, cooled to -10° C., of 10 g (0.072 mole) of 2-hydroxymethyl-4-methoxypyridine in 30 ml of dry chloroform over the course of 15 minutes. The solution is allowed to come to room temperature and is stirred for another one and a half hours. After the solvent and the excess thionyl chloride have been stripped off, colorless crystals are obtained and are recrystallized from isopropanol to yield the title compound [12.1 g (87%), m.p. 140° to 141° C., decomposition).

Provenance & Evidence