Hydrochloric Acid → Ethanone, 2-chloro-1-(3-pyridinyl)-, hydrochloride (1:1)

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Reaction Steps

To a solution of 100 g (0.83 moles) of 3-acetylpyridine in diethyl ether (1 L) was added of 1 M 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 moles) was added to a 5 L reactor equipped with a mechanical stirrer and dissolved with 1 M hydrogen chloride in acetic acid (830 mL). The mixture was stirred until a clear solution was obtained. N-chlorosuccinimide (111 g, 0.83 moles) was added, and a yellow mixture resulted. 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 80 g of N-chlorosuccinimide and additional product was collected to give a combined yield of 152 g. 1H NMR (DMSO-d6) δ 10.3 (br s, 1H), 9.27 (s, 1H), 8.96 (d, J=5.1Hz, 1H), 8.62 (d, J=9.9 Hz, 1H), 7.89 (m, 1H), 5.30 (s, 2H); MS (EI) m/z 155 (M+).

Provenance & Evidence