Hydrochloric Acid → 1-(Pyridin-3-yl)ethan-1-amine

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Reaction Steps

To a solution of 3-acetylpyridine (82.6 mmol) in methanol (200 mL) was added ammonium acetate (1.03 mol) in one portion at room temperature. After the mixture was stirred for 20 min, sodium cyanoborohydride (57.8 mmol) was added. After being stirring for one day, 6 M hydrochloric acid was added. The resulting solution was washed with diethyl ether, and then the aqueous phase was basified to pH=10 with potassium hydroxide. The liberated amine was extracted with chloroform, and the combined organic extracts were dried over anhydrous sodium sulfate. After removal of the solvent under reduced pressure, the crude amine was obtained as a colorless oil, which was further purified by distillation under reduced pressure. 1H NMR (300 MHz, CDCl3), d: 8.552 (d, 1H), 8.453 (dd, 1H), 7.678 (m, 1H), 7.206-7.261 (m, 1H), 4.148 (q, 1H), 1.378 (d, 3H).

Provenance & Evidence