1-(2,6-Dichlorophenyl)-5-(2,4-difluorophenyl)-7-methoxy-2(1H)-quinolinone → 1-(2,6-Dichlorophenyl)-5-(2,4-difluorophenyl)-7-hydroxy-2(1H)-quinolinone

HRID 394062Notes

Reaction equation

HRID 394062 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[F:28])[CH:15]=[C:16]([O:19]C)[CH:17]=2)[CH:12]=[CH: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[F:28])[CH:15]=[C:16]([OH:19])[CH:17]=2)[CH:12]=[CH:11][C:10]1=[O:29]

Participants

3

Reactant 2

HCID 226478721-(2,6-Dichlorophenyl)-5-(2,4-difluorophenyl)-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 226481861-(2,6-Dichlorophenyl)-5-(2,4-difluorophenyl)-7-hydroxy-2(1H)-quinolinone

Procedure

1-(2,6-Dichlorophenyl)-5-(2,4-difluorophenyl)-7-hydroxy-2(1H)-quinolinone was prepared from 1-(2,6-dichlorophenyl)-5-(2,4-difluorophenyl)-7-methoxy-2(1H)-quinolinone (INTERMEDIATE 4) by a procedure analogous to that described in INTERMEDIATE 3. Mass spectrum (ESI) 418.0 (M+1). 1H NMR (500 MHz, CDCl3): δ 7.57 (d, J=8 Hz, 1H); 7.47 (d, J=7.5 Hz, 2H); 7.33 (m, 2H); 7.02 (m, 2H); 6.96 (s, 1H); 6.52 (d, J=9.5, 1H); 6.01 (s, 1H).

Sources & evidence

ORD record
ord-4bd3a42d20c2463ba3e4aac7d508fb3d
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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