Hydrochloric Acid → 5-Fluoro-2-(4-fluorophenoxy)nicotinic acid

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of methyl 5-fluoro-2-(4-fluorophenoxy)nicotinate (step 1, 2.63 g, 9.9 mmol) in methanol (50 mL) was added 2 N sodium hydroxide aqueous solution (10 mL). The reaction mixture was stirred at 40° C. for 3 h. After cooling, the pH value was adjusted to 4.0 by the addition of 2 N hydrochloric acid. The mixture was diluted with water (100 mL), and extracted with dichloromethane (100 mL×3). The combined organic layer was washed with brine (100 mL), dried (sodium sulfate), and concentrated to afford 2.26 g (91%) of the title compound as off white solids: 1H-NMR (CDCl3) δ 8.25 (1H, dd, J=7.5, 3.1 Hz), 8.16 (1H, d, J=3.1 Hz), 7.16–7.13 (4H, m); MS (ESI) m/z 252 (M+H)+.

Provenance & Evidence