Hydrochloric Acid → 4-(1-Hydroxy-1-methylethyl)-6-(trifluoromethyl)pyridine-2-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(1-hydroxy-1-methylethyl)-6-(trifluoromethyl)pyridine-2-carbonitrile (0.088 g, 0.38 mmol, from Step C) in ethanol (4 mL) was added 1.0M sodium hydroxide in water (1.5 mL, 1.5 mmol) and the reaction was heated to 90° C. for 20 minutes. Upon cooling to room temperature, the reaction was acidified by the addition of 1N HCl to achieve pH 5 and the ethanol was removed in vacuo. The remaining aqueous mixture was extracted with ethyl acetate (3×). The combined extracts were dried over sodium sulfate, decanted and concentrated to afford product, used without further purification (80 mg, 84%). 1H NMR (400 MHz, CD3OD) δ 8.43 (d, J=1.6 Hz, 1H), 8.10 (d, J=1.6 Hz, 1H), 1.57 (s, 6H); 19F NMR (376 MHz, CD3OD) 5-69.39 (s); LCMS (M+H)+: 250.1.

Provenance & Evidence