Benzyl Bromide → N-benzyl-3-hydroxy-2-phenylpyridinium bromide

Participants

Reaction Steps

To a flame dried round bottom flask equipped with a nitrogen inlet and a condenser was introduced 1.3 gm. (7.59 mmol) 2-phenyl-3-hydroxypyridine, 3.25 gm. 2.26 ml (18.96 mmol) benzylbromide. The contents were dissolved in 30 ml of acetonitrile and the reaction mixture was heated under reflux for a period of 18 hours. The mixture was allowed to cool to room temperature and evaporated in vacuo. The residue was taken up in chloroform followed by treatment with ether to afford a solid precipitate. Upon filtration there was obtained 2.09 gm (81%) of 1-phenylmethyl-2-phenyl-3-hydroxypyridinium bromide. 1H NMR (CDCl3, 400 MHz) δ 8.70 (d, 1H), 8.25 (d, 1H), 7.50 (m, 2H), 7.40 (m, 2H), 7.30–7.20 (m, 5H), 6.90 (d, 2H), 5.60 (s, 2H) ppm. Mass spectrum APCI m/z 262.

Provenance & Evidence