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

HRID 1700644Notes

Reaction equation

HRID 1700644 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](=O)[CH2:36][CH3:37]>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]([CH2:36][CH3:37])[C:11]=2[C:10](=[O:26])[CH2:9]1

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 131561-Bromo-2-butanoneHCID 117288815-(2-Chlorophenyl)-1-[2-(4-methylphenylsulfonyl)hydrazino]cyclohexen-3-one

Product 1

HCID 183173627-(2-Chlorophenyl)-4-ethyl-5,6,7,8-tetrahydrocinnolin-5-oneYield 43%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5-(2-chlorophenyl)-1-[2-(4-methylphenylsulfonyl)hydrazino]cyclohexen-3-one (1.56 g), anhydrous potassium carbonate (0.72 g), 1-bromobutan-2-one (0.785 g) and methanol (30 ml) was stirred at room temperature for 2.5 hours. To the mixture was added anhydrous potassium carbonate (0.72 g), and the mixture was stirred at room temperature 1.5 hours and refluxed for 30 minutes. 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-ethyl-5,6,7,8-tetrahydrocinnolin-5-one (0.492 g) as oil.

Workup

  1. stirringthe mixture was stirred at room temperature 1.5 hours
  2. temperaturerefluxed for 30 minutes
  3. customUnder reduced pressure, the solvent was evaporated
  4. extractionthe residue was extracted with ethyl acetate
  5. concentrationThe organic layer was concentrated
  6. customthe residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-03bb0777e9bb4320a5717075a1517d5c
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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