Sodium Bicarbonate → 1-(2-Methyl-pyridin-4-yl)-2-phenyl-ethanone

Participants

Reaction Steps

3-(2-Methyl-pyridin-4-yl)-3-oxo-2-phenyl-propionitrile (1.02 g, 4.3 mmol) was suspended in HBr (48%, 10 mL) and heated to reflux overnight. The mixture was poured onto ice (20 g), was made alkaline (pH=11) by addition of NaHCO3 (satd.), and extracted with ethyl acetate. The combined organic layers were combined and dried (Na2SO4). After evaporation of the solvent, the title compound (233 mg, 26%) was isolated from the residue by column chromatography (silica gel, heptane:ethyl acetate=100:0-50:50). 1H NMR (300 MHz, DMSO-D6) 8.66 (1H, d), 7.78 (1H, s), 7.69 (1H, d), 7.35-7.24 (5H, m), 4.43 (2H, s), 2.57 (3H, s); MS (m/e)=212.1 [MH+].

Provenance & Evidence