61889-48-3

350-03-8

61889-48-3

Example 5 Synthesis of 3-(2-chloroacetyl)pyridine hydrochloride: 3-Acetylpyridine (100 g, 0.83 mol) was dissolved in ether (1 L) under rapid stirring conditions, and an ether solution of 1N hydrogen chloride (950 mL) was slowly added. The solid produced by the reaction was filtered, washed with ether and dried to give the hydrochloride intermediate (129 g, 0.83 mol). This hydrochloride intermediate was transferred to a 5L reactor fitted with a mechanical stirrer, dissolved with a solution of acetic acid in 1N HCl (830 mL) and stirred until the solution was clarified. Subsequently, N-chlorosuccinimide (111 g, 0.83 mol) was added and the reaction mixture was yellow in color. The reaction solution was stirred at room temperature for 18 h. The reaction solution gradually transformed into a colorless suspension. The solid product was collected by filtration and washed with ether. The filtrate was further treated with N-chlorosuccinimide (80 g, 0.6 mol) overnight to recover additional product. The final white solid product 3-(2-chloroacetyl)pyridine hydrochloride (152 g, 95% yield) was obtained. The structure of the product was confirmed by 1H-NMR (300 MHz, DMSO-d6) and mass spectrometry (EI): 1H-NMR 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+).