Hydrochloric Acid → 2-Chloro-1-(pyridin-3-yl)ethan-1-one--hydrogen chloride (1/1)

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Reaction Steps

To a solution of 3-acetylpyridine (100 g, 0.83 moles) in diethyl ether (1 L) was added of 1 N hydrogen chloride in ether (950 mL) with rapid stirring. The precipitated solids were filtered, washed with ether and dried. The hydrochloride salt (129 g, 0.83 mol) was added to a 5 L reactor equipped with a mechanical stirrer and dissolved with 1 N HCl in acetic acid (830 mL). The mixture was stirred until a clear solution was obtained, then N-chlorosuccinimide (111 g, 0.83 mol) was added, resulting in a yellow mixture. The solution was stirred at room temperature for 18 hours, gradually becoming a colorless suspension. The solids were collected by filtration and washed with ether; the filtrate was treated overnight with N-chlorosuccinimide (80 g, 0.6 mole) and additional product was collected to yield a white solid (152 g, 95%). 1H-NMR (300 MHz, DMSO-d6) δ 10.3 (br s, 1H), 9.27 (s, 1H), 8.96 (d, 1H, J=5.1 Hz), 8.62 (d, 1H, J=9.9 Hz), 7.89 (m, 1H), 5.30 (s, 2H); MS (EI) m/z 155 (M+).

Provenance & Evidence