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

HRID 394061Notes

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][CH3:20])[CH:17]=2)[CH2:12][CH2:11][C:10]1=[O:29].BrN1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[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][CH3:20])[CH:17]=2)[CH:12]=[CH:11][C:10]1=[O:29]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 11 mg of 1-(2,6-dichlorophenyl)-5-(2,4-difluorophenyl)-3,4-dihydro-7-methoxy-2(1H)-quinolinone in 2.5 mL of CCl4 was added 12 mg of N-bromosuccinimide and 6 mg of 2,2′azobis(2-methylpropionitrile). The mixture was heated to 80° C. for 1.5 h, then concentrated and purified by preparative thin-layer chromatography, eluting with 1:1 hexanes-EtOAc, to yield 1-(2,6-Dichlorophenyl)-5-(2,4-difluorophenyl)-7-methoxy-2(1H)-quinolinone. Mass spectrum (ESI) 432.1 (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).

Workup

concentrationconcentrated
custompurified by preparative thin-layer chromatography
washeluting with 1:1 hexanes-EtOAc

Sources & evidence

ORD record: ord-2d663d91314b4ad6828eb3bd85626f1c
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06809199B2

Reaction notes

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