N-(3-Chlorophenyl)-2-methyl-3-phenylacrylamide → 7-Chloro-3-methyl-1H-quinolin-2-one

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

To a solution of N-(3-chlorophenyl)-2-methyl-3-phenylacrylamide (2.5 g, 9.2 mmol) in chlorobenzene (50 mL) is added AlCl3 (6.2 g, 46 mmol). The solution is heated to 120° C. After 4 hours the solution is poured onto ice. The solution is filtered. The organic layer is washed with 1N HCl, H2O and saturated NaCl. The crude product is purified by column chromatography eluting with 2% MeOH/CH2Cl2. The title compound is obtained as a white solid (1.5 g, 7.74 mmol). 1H NMR (d6-DMSO, 300 MHz) δ11.82 (bs, 1H), 7.73 (s, 1H), 7.52 (m, 1H), 7.21 (m, 2H), 2.08 (s, 3H).

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