Phenacyl bromide → 7-(2-Chlorophenyl)-4-phenyl-5,6,7,8-tetrahydrocinnolin-5-one

HRID 1700646Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:13][C:12]([NH:14][NH:15]S(C2C=CC(C)=CC=2)(=O)=O)=[CH:11][C:10](=[O:26])[CH2:9]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:34][C:35]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=O>CO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:13][C:12]2[N:14]=[N:15][CH:34]=[C:35]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C:11]=2[C:10](=[O:26])[CH2:9]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 5-(2-chlorophenyl)-1-[2-(4-methylphenylsulfonyl)hydrazino]cyclohexen-3-one (1.35 g), anhydrous potassium carbonate (1.19 g), 2-bromoacetophenone (0.893 g) and methanol (30 ml) was stirred at 80° C. for 3 hours. Under reduced pressure, the solvent was evaporated, and the residue was extracted with ethyl acetate. The organic layer was concentrated, and the residue was purified with silica gel column chromatography to give 7-(2-chlorophenyl)-4-phenyl-5,6,7,8-tetrahydrocinnolin-5-one (0.46 g) as oil.

Workup

customUnder reduced pressure, the solvent was evaporated
extractionthe residue was extracted with ethyl acetate
concentrationThe organic layer was concentrated
customthe residue was purified with silica gel column chromatography

Sources & evidence

ORD record: ord-f7f0293a27614ca4a6fddaa276e80531
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06350749B1

Reaction notes

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