Dichloromethane → 5,7-dichloro-3-(4-hydroxy-3-nitro-phenyl)-3-methyl-1H-quinoline-2,4-dione

Participants

Reaction Steps

The objective compound was prepared by the same procedure for the example 13, using a 5,7-dichloro-3-(4-methoxy-3-nitro-phenyl)-3-methyl-1H-quinoline-2,4-dione (0.12 g, 0.30 mmol) and BBr3 (0.90 mL, 1.0 M dichloromethane solution). After normal workup, the objective compound (50 mg, 48%) was obtained as pale yellow solid by a flash column chromatography (dichloromethane:methanol=30:1): 1H NMR (200 MHz, DMSO-d6) δ 1.58 (s, 3H, CH3), 7.05-7.09 (m, 2H, ArH), 7.14-7.31 (m, 2H, ArH), 7.61 (d, J=2.4 Hz, 1H, ArH); m.p. 239-240° C.; MS(EI) m/e 380 [M+], 193, 165, 135; HRMS m/e cacld. for C16H10N2O5Cl2 379.9967, found 379.9968.

Provenance & Evidence