Hydrochloric Acid → 4-Methyl-6-phenylpyridazin-3(2H)-one

関与物質

反応手順

(Csende, F et al. Synthesis, 1995, 1240-1242) 7.0 g (35 mmol) of 13 was dissolved in 30 ml of acetonitrile in a 250 ml single-necked round bottom flask. 11.3 g (84 mmol, 2.4 equiv) of anhydrous copper (H) chloride Was added to the solution and the reaction mixture was heated to reflux for 2 hours. To control the HCl gas that formed during the course of the reaction, a NaOH solution was used to absorb the HCl that escapes from dry tube. The reaction mixture was cooled to ambient temperature, and placed into an ice-water bath. 150 mL of ice-water was added to quench the reaction. The mixture was stirred vigorously for 10 minutes to give a gray precipitate and blue liquid containing copper (I) chloride. The precipitate was then collected by filtration (pH of the filtrate is 0-1) and washed first with 1N HCl (100 mL), then with Milli-Q water (5×100 mL). To remove remaining copper by-products, the filter cake was stirred in 1N HCl (150 mL) for 0.5 h and then filtered. The filter cake was washed with water until the filtrate is at pH 7 (approximately 7 washes). The solid was dried over a medium flit sintered glass funnel in vacuo to give 14 as a light gray powder in 93.8% yield, 1H NMR (DMSO-d6): δ 7.95 (s, 1H), 7.85 (d, J=7.5 Hz; 2H), 7.47 (m, 2H), 7.43 (m, 1H), 2.13 (s, 3H). HPLC (tr/purity): 21.48 min, >97%; ESI m/z (MeOH) 187.36 (MH+).

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