2-(2-Hydroxyethyl)pyridine → Pyridine, 2-(2-chloroethyl)-, hydrochloride

Participants

Reaction Steps

Thionyl chloride (SOCl2, 6.2 ml) in chloroform (15 ml) was added dropwise to an ice chilled solution of 2-(2-hydroxyethyl)pyridine (Aldrich, 10 g, 81 mmol in chloroform (10 ml. After addition was complete, the reaction mixture was stirred for 15 hours. The solvent and excess thionyl chloride were removed on a vacuum rotary evaporator followed by exposure to high vacuum (90 minutes, 0.5 mm Hg, 80° C.) Recrystallization of the crude brown solid from isopropanol-isopropyl ether yielded 10.8 g of pure 2-(2-pyridinyl)ethyl chloride hydrochloride (mp. 124°-125° C., lit. mp., about 120° C., Gump et al., U.S. Pat. No. 2,533,243; Chem. Abstr., 1950, 45, p. 4271c) as light tan beads.

Provenance & Evidence