1-(2,6-Dichlorophenyl)-5-(2,4-difluorophenyl)-3,4-dihydro-7-hydroxy-2(1H)-quinolinone → 5-(2-Chlorophenyl)-1-(2,6-dichlorophenyl)-3,4-dihydro-7-hydroxy-2(1H)-quinolinone

HRID 394064Notes

Reaction equation

HRID 394064 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]([O:18]C)[CH:15]=[C:14]2[C:9]=1[CH2:10][CH2:11][C:12](=[O:28])[N:13]2[C:20]1[C:25]([Cl:26])=[CH:24][CH:23]=[CH:22][C:21]=1[Cl:27].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]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]([OH:18])[CH:15]=[C:14]2[C:9]=1[CH2:10][CH2:11][C:12](=[O:28])[N:13]2[C:20]1[C:21]([Cl:27])=[CH:22][CH:23]=[CH:24][C:25]=1[Cl:26]

Participants

3

Reactant 2

HCID 226480931-(2,6-Dichlorophenyl)-5-(2,4-difluorophenyl)-3,4-dihydro-7-hydroxy-2(1H)-quinolinoneHCID 226481195-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-3,4-dihydro-7-methoxy-2(1H)-quinolinone2×

Product 1

HCID 226479955-(2-Chlorophenyl)-1-(2,6-dichlorophenyl)-3,4-dihydro-7-hydroxy-2(1H)-quinolinone

Procedure

5-(2-Chlorophenyl)-1-(2,6-dichlorophenyl)-3,4-dihydro-7-hydroxy-2(1H)-quinolinone was prepared from 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-3,4-dihydro-7-methoxy-2(1H)-quinolinone (INTERMEDIATE 6) by a procedure analogous to that described in INTERMEDIATE 3 Mass spectrum (ESI) 418.1 (M+1). 1H NMR (500 MHz, CDCl3): δ 7.43-7.52 (m, 2H); 7.22-7.40 (m, 4H); 6.38 (d, J=2.5 Hz, 1H); 5.82 (d, J=2.5 Hz, 1H); 2.58-2.85 (m, 4H).

Sources & evidence

ORD record
ord-3fa3766e3142407093c8878f252b555c
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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