Potassium Cyanide → 3-Pyridineacetonitrile, 6-(trifluoromethyl)-

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Reaction Steps

To a solution of Example 85C (2.1 g, 1.08 mmol) in 40 mL of ethanol and 15 mL of water was added KCN (0.84 g, 12.9 mmol). The mixture was refluxed for 6 hours, and then cooled to room temperature. Most of the ethanol was removed under vacuo and the residue was diluted with 25 mL of water. The resulting mixture was extracted with ethyl acetate (100 mL×3). The combined organic layers were dried over Na2SO4, filtered, and concentrated. The crude product was purified by silica gel column (petroleum ether:ethyl acetate=20:1) to afford the title compound (1.55 g, 64.7%). 1H NMR (400 MHz, CDCl3): δ 8.78 (s, 1H), 7.77-7.94 (m, 2H), 3.84 (s, 2H).

Provenance & Evidence