Nitrogen → 3-chloro-4-(chloromethyl)pyridine hydrochloride

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Reaction Steps

Solid 3-chloro-4-hydoxymethylpyridine (33.8 g, 0.235 mol) was added cautiously over 8 min to stirred thionyl chloride (72 ml, 0.706 mol) cooled in an ice bath and under a stream of N2. After addition the yellow solution was heated in an oil bath at 50° and protected under a tube of Drierite. After 30 min the solution was removed from the oil bath, allowed to cool to ambient temperature, and poured into a flask of stirred anhydrous ether (1,000 ml).

Provenance & Evidence