Hexane → 5,7-dichloro-3-(4-methoxy-phenyl)-3-methyl-1H-quinoline-2,4-dione

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Reaction Steps

The objective compound was prepared by the same procedure for the example 1, using a 4,6-dichloro-2-[2-(4-methoxy-phenyl)-propionylamino]-benzoic acid methyl ester (1.44 g, 3.77 mmol) and LiHMDS (11.0 mmol, 1M solution in THF). After normal workup, the pure objective compound (0.55 g, 42%) was obtained as yellow solid by a flash column chromatography (n-hexane:EtOAc=10:1): 1H NMR (200 MHz, CDCl3) δ 1.52 (s, 3H, CH3), 3.67 (s, 3H, CO2CH3), 6.89 (d, J=8.9 Hz, 2H, ArH), 6.99-7.08 (m, 3H, ArH), 7.23 (d, J=1.9 Hz, 1H, ArH), 11.25 (s, 1H, NH); m.p. 210-212° C.; MS(EI) m/e 349 [M+], 162, 134; HRMS m/e cacld. for C17H13NO3Cl2 349.0272, found 349.0278.

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