1-(2,6-dichlorophenyl)-3,4-dihydro-5-(4-fluoro-2-methylphenyl)-7-methoxy-2(1H)-quinolinone → 1-(2,6-Dichlorophenyl)-3,4-dihydro-5-(4-fluoro-2-methylphenyl)-7-hydroxy-2(1H)-quinolinone

HRID 394070Notes

Reaction equation

HRID 394070 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:18]2[C:13](=[C:14]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=3[CH3:28])[CH:15]=[C:16]([O:19]C)[CH:17]=2)[CH2:12][CH2:11][C:10]1=[O:29].ClC1C=CC=C(Cl)C=1N1C2C(=C(C3C=CC(F)=CC=3F)C=C(O)C=2)CCC1=O>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:18]2[C:13](=[C:14]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=3[CH3:28])[CH:15]=[C:16]([OH:19])[CH:17]=2)[CH2:12][CH2:11][C:10]1=[O:29]

Participants

3

Reactant 2

HCID 226479211-(2,6-dichlorophenyl)-3,4-dihydro-5-(4-fluoro-2-methylphenyl)-7-methoxy-2(1H)-quinolinone2×HCID 226480931-(2,6-Dichlorophenyl)-5-(2,4-difluorophenyl)-3,4-dihydro-7-hydroxy-2(1H)-quinolinone

Product 1

HCID 226480121-(2,6-Dichlorophenyl)-3,4-dihydro-5-(4-fluoro-2-methylphenyl)-7-hydroxy-2(1H)-quinolinone

Procedure

1-(2,6-Dichlorophenyl)-3,4-dihydro-5-(4-fluoro-2-methylphenyl)-7-hydroxy-2(1H)-quinolinone was prepared from 1-(2,6-dichlorophenyl)-3,4-dihydro-5-(4-fluoro-2-methylphenyl)-7-methoxy-2(1H)-quinolinone (INTERMEDIATE 12) by a procedure analogous to that described in INTERMEDIATE 3. Mass spectrum (ESI) 416.0 (M+1). 1H NMR (500 MHz, CDCl3): δ 7.56 (m, 3H); 7.44 (m, 1H); 7.37 (m, 1H); 7.02 (m, 2H); 6.76 (s, 1H); 6.58 (d, J=10 Hz, 1H); 6.01 (s, 1H); 3.73 (s, 3H).

Sources & evidence

ORD record
ord-14bf0d16aa5a4fb4a82956ac410e2a07
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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