Hydrochloric Acid → 2-Chloro-3-iodo-4-methylpyridine

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-chloro-4-methylpyridin-3-amine (1.0 g, 7.0 mmol) and concentrated hydrochloric acid (4.4 mL) was cooled to 0° C. and a solution of sodium nitrite (0.5 g, 7.5 mmol) in water (8 mL) was added dropwise. The mixture was stirred for 1 hour at 0° C. and then was added dropwise to a stirred solution of potassium iodide (1.6 g, 9.6 mmol) in water (9 mL). The mixture was warmed to ambient temperature and stirred overnight. The mixture was extracted with diethyl ether and the organic phase was washed with aqueous sodium thiosulphate, brine, dried (MgSO4) and evaporated in vacuo. The crude product was recrystallized from hexane to give the title compound (0.88 g, 47%) as a white solid.

Provenance & Evidence