Dichloromethane → 5,7-dichloro-3-(4-methoxy-3-nitro-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 13, using a 4,6-dichloro-2-[2-(4-methoxy-3-nitro-phenyl)-propionylamino]-benzoic acid methyl ester (0.20 g, 0.47 mmol) and LiHMDS (1.40 mmol, 1M THF solution). After normal workup, the objective compound (120 mg, 71%) was obtained as yellow solid by a flash column chromatography (dichloromethane:methanol=30:1): 1H NMR (200 MHz, DMSO-d6) δ 1.60 (s, 3H, CH3), 3.86 (s, 3H, OCH3), 7.05 (d, J=2.0 Hz, 1H, ArH), 7.29-7.37 (m, 2H, ArH), 7.61 (d, J=2.0 Hz, 1H, ArH); m.p. 255-256° C.; MS(EI) m/e 394 [M+], 207, 132, 119; HRMS m/e cacld. for C17H12N2O5Cl2 394.0123, found 394.0114.

Provenance & Evidence