Reaction #66912

Reaction equation

Compound 22

7-Benzyloxy-2-(2-fluorophenyl)-6-methoxyquinolin-4-one

compound 40

2-(2-Fluorophenyl)-5,6-dihydroxyquinolin-4-one

→

43

Yield 61.3%

2-(2-Fluorophenyl)-7-hydroxy-6-methoxyquinolin-4-one

Yield 61.3%

Conditions

Workup

1. 1
   Otherto react in the same manner

Procedure

Compound 22 (0.3 g, 0.80 mmol) was allowed to react in the same manner as described in the preparation of compound 40 to give 43. White solid; yield: 61.3%; mp 277-279° C.; MS (EI, 70 eV): m/z 285 (M+); IR (KBr): 1622.13 (C═O) cm−1; 1H-NMR (DMSO-d6 200 MHz): δ 3.82 (s, 3H), 6.04 (s, 1H), 7.01 (s, 1H), 7.32-7.50 (m, 3H), 7.50-7.67 (m, 2H), 10.22 (s, 1H), 11.68 (s, 1H); 13C-NMR (DMSO-d6, 50 MHz): δ 55.52, 102.72, 105.37, 108.20, 116.28 (d, J=22.5 Hz), 118.07, 122.94, 124.92, 130.75, 131.99 (d, J=7.95 Hz), 136.45, 143.61, 146.58, 151.59, 158.98 (d, J=246.9 Hz), 175.30; Anal. calcd for C16H12FNO3: C, 67.36; H, 4.24; N, 4.91. Found: C, 67.37; H, 4.26; N, 4.90.

Source