2-Acetyl-6-methylpyridine → 1-(6-Methylpyridin-2-yl)ethan-1-amine

Participants

Reaction Steps

To a solution of 2-acetyl-6-methylpyridine (4.7 g, 34.8 mmol) in anhydrous methanol (100 ml) was added ammonium acetate (26.8 g, 348 mmol) and sodium cyanoborohydride (1.75 g, 27.8 mmol) and the resulting mixture stirred at RT overnight. The mixture was evaporated and the residue dissolved in water and basified by the addition of KOH and extracted with DCM (×3). The DCM layers were combined and washed with sat. NaCl, dried over MgSO4, filtered and evaporated. The residue was purified by column chromatography on silica to afford the title compound (i-14) (eluent: 5% MeOH in DCM) to give 2.8 g (59%) as a clear oil. 1H NMR (CDCl3): 1.41 (d, J 6.7 Hz, 3H), 1.78 (brs, 2H), 2.54 (s, 3H), 4.21 (q, J 6.7 Hz, 1H), 6.99 (d, J 7.6 Hz, 1H), 7.09 (d, J 7.7 Hz, 1H), 7.52 (m, 1H).

Provenance & Evidence