Potassium Carbonate → 4-Phenylpyridin-2-ol

Participants

Reaction Steps

A solution of 4-phenylpyridine-1-oxide (2.00 g, 0.012 mol) in acetic anhydride (6 mL) was heated at reflux for 48 hours. The reaction mixture was cooled to ambient temperature, diluted with ethyl acetate (80 mL) and washed with saturated aqueous sodium bicarbonate (2×15 mL) and brine (15 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was dissolved in methanol (20 mL) and potassium carbonate (0.32 g, 0.002 mol) was added to the solution. The reaction mixture was stirred at ambient temperature for 1 hour, then diluted with chloroform (100 mL) and filtered through Celite. The filtrate was concentrated in vacuo. The residue was dissolved in a mixture of methanol/chloroform 1/10 (30 mL). The title compound was precipitated with the addition of hexanes (30 mL) as a white solid which was collected by filtration (1.20 g, 60%): 1H NMR (300 MHz, DMSO-d6) δ 7.66-7.62 (m, 2H), 7.48-7.37 (m, 4H), 6.51 (d, J=1.2 Hz, 1H), 6.44 (dd, J=6.7, 1.8 Hz, 1H); MS (ES+) m/z 172.5 (M+1).

Provenance & Evidence