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

HRID 1700646
Notes
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Reaction equation

HRID 1700646 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 11430Potassium CarbonateHCID 117288815-(2-Chlorophenyl)-1-[2-(4-methylphenylsulfonyl)hydrazino]cyclohexen-3-one

Product 1

HCID 183177727-(2-Chlorophenyl)-4-phenyl-5,6,7,8-tetrahydrocinnolin-5-oneYield 39.8%

Reagents, catalysts & solvents 1

HCID 887Methanol
Solvent

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

  1. customUnder reduced pressure, the solvent was evaporated
  2. extractionthe residue was extracted with ethyl acetate
  3. concentrationThe organic layer was concentrated
  4. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes