5-(2-Chloro-5-fluorophenyl)-1-(2,6-dichlorophenyl)-3,4-dihydro-7-methoxy-2(1H)-quinolinone → 5-(2-Chloro-5-fluorophenyl)-1-(2,6-dichlorophenyl)-3,4-dihydro-7-hydroxy-2(1H)-quinolinone

HRID 394068Notes

Reaction equation

HRID 394068 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH:18]=[C:17]([O:19]C)[CH:16]=[C:15]2[C:10]=1[CH2:11][CH2:12][C:13](=[O:29])[N:14]2[C:21]1[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:22]=1[Cl:28].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][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[CH:18]=[C:17]([OH:19])[CH:16]=[C:15]2[C:10]=1[CH2:11][CH2:12][C:13](=[O:29])[N:14]2[C:21]1[C:22]([Cl:28])=[CH:23][CH:24]=[CH:25][C:26]=1[Cl:27]

Participants

3

Reactant 2

HCID 226480755-(2-Chloro-5-fluorophenyl)-1-(2,6-dichlorophenyl)-3,4-dihydro-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 226480905-(2-Chloro-5-fluorophenyl)-1-(2,6-dichlorophenyl)-3,4-dihydro-7-hydroxy-2(1H)-quinolinone

Procedure

5-(2-Chloro-5-fluorophenyl)-1-(2,6-dichlorophenyl)-3,4-dihydro-7-hydroxy-2(1H)-quinolinone was prepared from 5-(2-chloro-5-fluorophenyl)-1-(2,6-dichlorophenyl)-3,4dihydro-7-methoxy-2(1H)-quinolinone (INTERMEDIATE 10) by a procedure analogous to that described in INTERMEDIATE 3. Mass spectrum (ESI) 438.1 (M+1). 1H NMR (500 MHz, CDCl3): δ 7.49 (d, J=7.5 Hz, 2H); 7.36 (t, J=8 Hz, 1H); 7.27 (m, 2H); 7.07 (m, 1H); 6.38 (s, 1H); 5.83 (s, 1H); 2.73 (m, 4H).

Sources & evidence

ORD record
ord-bf59efd875b94be1b3cd80a069a0b342
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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