Azobisisobutyronitrile → 5-(2-Chlorophenyl)-1-(2,6-dichlorophenyl)-7-methoxy-2(1H)-quinolinone

HRID 394065Notes

Reaction equation

HRID 394065 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][CH3:19])[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].BrN1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.ClC1C=CC=C(Cl)C=1N1C2C(=C(C3C=CC(F)=CC=3F)C=C(OC)C=2)C=CC1=O>>[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][CH3:19])[CH:15]=[C:14]2[C:9]=1[CH:10]=[CH: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

5

Reactant 4

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 226478721-(2,6-Dichlorophenyl)-5-(2,4-difluorophenyl)-7-methoxy-2(1H)-quinolinoneHCID 226481195-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-3,4-dihydro-7-methoxy-2(1H)-quinolinone2×

Product 1

HCID 226479055-(2-Chlorophenyl)-1-(2,6-dichlorophenyl)-7-methoxy-2(1H)-quinolinone

Procedure

5-(2-Chlorophenyl)-1-(2,6-dichlorophenyl)-7-methoxy-2(1H)-quinolinone was prepared from 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-3,4-dihydro-7-methoxy-2(1H)-quinolinone (INTERMEDIATE 6), N-bromosuccinimide, and 2,2′-azobis(2-methylpropionitrile) by a procedure analogous to that described in INTERMEDIATE 4. Mass spectrum (ESI) 430.0 (M+1). 1H NMR (500 MHz, CDCl3): δ 7.53-7.62 (m, 3H); 7.30-7.49 (m, 5H); 6.77 (d, J=2.0 Hz, 1H); 6.61 (d, J=9.5 Hz, 1H); 6.03 (d, J=2.5 Hz, 1H); 3.74 (s, 3H).

Sources & evidence

ORD record
ord-64fb516c00c6437aa93944061b9e4723
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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