Hexane → 3-(3-hydroxy-phenyl)-5,7-dichloro-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 3-(3-benzyloxy-phenyl)-5,7-dichloro-3-methyl-1H-quinoline-2,4-dione (0.26 g, 0.60 mmol) and BBr3 (1.20 mL, 1.0 M dichloromethane solution). After normal workup, the objective compound (0.18 g, 90%) was obtained as yellow solid by a flash column chromatography (n-hexane:EtOAc=5:1): 1H NMR (200 MHz, CDCl3+DMSO-d6) δ 1.62 (s, 3H, CH3), 6.57-6.71 (m, 3H, ArH), 6.98-7.12 (m, 3H, ArH), 9.17 (s, 1H, OH), 11.07 (s, 1H, NH); m.p. 248° C. (decomp.); MS(EI) m/e 335 [M+], 148, 91.

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