Potassium Carbonate → 7-(2-Chlorophenyl)-4-(4-chlorophenyl)-5,6,7,8-tetrahydrocinnolin-5-one

HRID 1700681Notes

Reaction equation

HRID 1700681 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.Br[CH2:28][C:29]([C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=1)=O.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[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:28]=[C:29]([C:31]3[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=3)[C:11]=2[C:10](=[O:26])[CH2:9]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 68303p-Chlorophenacyl bromideHCID 117288815-(2-Chlorophenyl)-1-[2-(4-methylphenylsulfonyl)hydrazino]cyclohexen-3-one

Product 1

HCID 183175497-(2-Chlorophenyl)-4-(4-chlorophenyl)-5,6,7,8-tetrahydrocinnolin-5-oneYield 10.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-(2-chlorophenyl)-1-[2-(4-methylphenylsulfonyl)hydrazino]cyclohexen-3-one (2.0 g), 2-bromo-4′-chloroacetophenone (1.6 g), anhydrous potassium carbonate (1.8 g) and ethanol (50 ml) was refluxed for 13 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. The resulting crystals were recrystallized from ethyl acetate-hexane to give 7-(2-chlorophenyl)-4-(4-chlorophenyl)-5,6,7,8-tetrahydrocinnolin-5-one (0.2 g) as colorless crystals.

Workup

  1. temperaturewas refluxed for 13 hours
  2. customUnder reduced pressure, the solvent was evaporated
  3. extractionthe residue was extracted with ethyl acetate
  4. concentrationThe organic layer was concentrated
  5. customthe residue was purified with silica gel column chromatography
  6. customThe resulting crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-48dfd72399954d4790cd3057fc61266d
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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