The synthesis of 2‐chloromethylpyridine from 2‐picoline‐<i>N</i>‐oxide

Abstract

Abstract Phosphoryl chloride reacts with 2‐picoline‐ N ‐oxide in the presence of triethylamine to give 2‐chloromethylpyridine in 90% conversion with 98% selectivity. Diethylchlorophosphate, ethyl chloroformate, chloroacetyl chloride and phosgene also react with 2‐picoline‐ N ‐oxide to give 2‐chloromethylpyridine in moderate yields. Other potential chlorinating agents, titanium tetrachloride, zinc chloride, magnesium chloride and sulfuryl chloride, did not convert 2‐picoline N ‐oxide into 2‐chloromethylpyridine.