Hexane → HCID 11716135, compound

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Reaction Steps

The objective compound was prepared by the same procedure for the example 13, using a 3-(4-hydroxy-3-methoxy-phenyl)-3-methyl-1H-quinoline-2,4-dione (120 mg, 0.40 mmol) and BBr3 (1.60 mL, 1.0 M solution in dichloromethane). After normal workup, the pure objective compound (71 mg, 62%) was obtained as pale yellow solid by a flash column chromatography (n-hexane:EtOAc=3:1): 1H NMR (200 MHz, DMSO-d6) δ 1.57 (s, 3H, CH3), 6.42 (dd, J=8.14, 2.03 Hz, 1H, ArH), 6.59-6.63 (m, 2H, ArH), 7.07 (t, J=7.73 Hz, 2H, ArH), 7.55 (t, J=7.32 Hz, 1H, ArH), 7.68 (d, J=7.32 Hz, 1H, ArH), 9.00 (br s, 1H, OH), 10.93 (br s, 1H, NH); m.p. 259-261° C.; MS(EI) m/e 283 [M+], 268, 255, 237; HRMS m/e cacld. for C16H13N1O4 283.0845, found 283.0849.

Provenance & Evidence