Sodium Azide → 6-Azidomethyl-3-benzyloxy-2-methylpyridine

Participants

Reaction Steps

A solution of 3-benzyloxy-6-chloromethyl-2-methylpyridine (8.02 g) and sodium azide (5.98 g) in 400 ml of ethanol is heated at 80° for 4 hours. The reaction mixture is cooled, filtered and evaporated to yield a residue which is partitioned between ice-cold 0.5N NaOH (150 ml) and ether (150 ml). The organic phase is dried over sodium sulfate and evaporated to yield 6-azidomethyl-3-benzyloxy-2-methylpyridine, NMR: δ(CDCl3) 2.47 (3H), 4.27 (2H), 4.95 (2H).

Provenance & Evidence