Ethanol → 6-(3,3,3-Trifluoropropyl)pyridine-3-carboxylic acid

Participants

Reaction Steps

To a solution of 6-(3,3,3-trifluoropropyl)pyridine-3-carbonitrile (Intermediate 208, 189 mg, 0.945 mmol) in EtOH (20 mL) was added potassium hydroxide (265 mg, 4.72 mmol). The solution was heated at 100 C for 6 h and then additional potassium hydroxide (53 mg, 0.94 mmol) added. After stirring for a further 3 h at 105 C, the reaction mixture was cooled to room temperature, evaporated to dryness and re-dissolved in water (20 mL). The solution was acidified to pH 3 with a 1M aq. HCl solution and extracted with EtOAc (3×25 mL). Combined organics were dried over magnesium sulfate and evaporated to dryness to afford the title compound as a light brown solid (183 mg, 89%). Method C HPLC-MS: MH+ requires m/z=220. Found: m/z=220, Rt=1.12 min (91%).

Provenance & Evidence