2-(2-Fluorophenyl)-5,6-dihydroxyquinolin-4-one → 2-(2-Fluorophenyl)-7-hydroxy-6-methoxyquinolin-4-one

HRID 38634Notes

Reaction equation

HRID 38634 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](=[O:26])[CH2:14][C:15]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[F:25])=[N:16]2)=[CH:11][C:10]=1[O:27][CH3:28])C1C=CC=CC=1.FC1C=CC=CC=1C1CC(=O)C2C(=CC=C(O)C=2O)N=1>>[F:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[C:15]1[CH2:14][C:13](=[O:26])[C:12]2[C:17](=[CH:18][C:9]([OH:8])=[C:10]([O:27][CH3:28])[CH:11]=2)[N:16]=1

Participants

3

Reactant 2

HCID 666593062-(2-Fluorophenyl)-5,6-dihydroxyquinolin-4-oneHCID 666595517-Benzyloxy-2-(2-fluorophenyl)-6-methoxyquinolin-4-one

Product 1

HCID 666591982-(2-Fluorophenyl)-7-hydroxy-6-methoxyquinolin-4-oneYield 61.3%

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.

Workup

  1. customto react in the same manner

Sources & evidence

ORD record
ord-9b0d2128d46546b9840eaa49168e1c25
Source dataset
uspto-grants-2013_09
Patent number
US08524740B2

Reaction notes

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