Hydrochloric Acid → 2-Oxo-1-phenyl-1,2-dihydropyridine-3-carboxylic acid

Participants

Reaction Steps

A mixture of methyl 2-oxo-1-phenyl-1,2-dihydropyridine-3-carboxylate (70 mg, 0.31 mmol) and LiOH (40 mg) in methanol (6 mL) and water (1 mL) was stirred at rt overnight. To the reaction mixture were added EtOAc (50 mL) and 1 N aq HCl (15 mL). The EtOAc layer was separated, dried over MgSO4, and concentrated in vacuo to afford the product (55 mg, 83%) as a light yellow solid. 1H NMR (DMF-d7) δ 11.77 (br s, 1H), 8.57 (dd, 1H, J=7.4, 2.0 Hz), 8.26 (dd, 1H, J=6.6, 1.6 Hz), 7.64-7.55 (m, 5H), 6.88 (t, 1H, J=7.0 Hz); MS (ESI+) m/z 216.2 (M+H)+.

Provenance & Evidence