Hydrochloric Acid → 4-(Methoxymethyl)-6-(trifluoromethyl)pyridine-2-carboxylic acid

Participants

Reaction Steps

To a solution of 4-(methoxymethyl)-6-(trifluoromethyl)pyridine-2-carbonitrile (0.36 g, 1.7 mmol, from Step C) in ethanol (20 mL) was added 1.0M sodium hydroxide in water (6.5 mL, 6.5 mmol) and the reaction was heated in an oil bath held at 90° C. for 4 hours. Upon cooling to room temperature, 1N HCl was added to achieve pH 2, and the product was extracted with ethyl acetate (3×). The combined extracts were dried over sodium sulfate, decanted and concentrated to afford a crystalline solid which was used without further purification. 1H NMR (300 MHz, CD3OD) δ 8.29 (s, 1H), 7.95 (s, 1H), 4.66 (s, 2H), 3.49 (s, 3H); 19F NMR (282 MHz, CD3OD) δ−69.56 (s); LCMS (M+H)+: 236.0.

Provenance & Evidence