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

HRID 1700647Notes

Reaction equation

HRID 1700647 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)[C:36]([F:39])([F:38])[F: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]([C:36]([F:39])([F:38])[F:37])[C:11]=2[C:10](=[O:26])[CH2:9]1

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 790083-Bromo-1,1,1-trifluoro-2-propanoneHCID 117288815-(2-Chlorophenyl)-1-[2-(4-methylphenylsulfonyl)hydrazino]cyclohexen-3-one

Product 1

HCID 183176067-(2-Chlorophenyl)-4-trifluoromethyl-5,6,7,8-tetrahydrocinnolin-5-oneYield 44.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 5-(2-chlorophenyl)-1-[2-(4-methylphenylsulfonyl)hydrazino]cyclohexen-3-one (2.74 g), anhydrous potassium carbonate (1.26 g) and methanol (30 ml) was added at room temperature 1-bromo-3,3,3-trifluoropropan-2-one (1.74 g), and the mixture was stirred at the same temperature for 0.5 hours. To the mixture was added anhydrous potassium carbonate (1.26 g), and the mixture was refluxed for 1 hour. Under reduced pressure, the solvent was evaporated, and the residue was extracted with ethyl acetate. The organic layer was concentrated, and the residue was dissolved in acetic acid (20 ml). To the solution was added concentrated sulfuric acid (1 ml), and the mixture was refluxed for 20 minutes. To the reaction solution was added water (120 ml), and the mixture was concentrated under reduced pressure. The residue was extracted with ethyl acetate, and the organic layer was washed with sodium hydrogen carbonate solution and concentrated. The residue was purified with silica gel column chromatography to give 7-(2-chlorophenyl)-4-trifluoromethyl-5,6,7,8-tetrahydrocinnolin-5-one (1.02 g) as oil.

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. customUnder reduced pressure, the solvent was evaporated
  3. extractionthe residue was extracted with ethyl acetate
  4. concentrationThe organic layer was concentrated
  5. dissolutionthe residue was dissolved in acetic acid (20 ml)
  6. additionTo the solution was added concentrated sulfuric acid (1 ml)
  7. temperaturethe mixture was refluxed for 20 minutes
  8. additionTo the reaction solution was added water (120 ml)
  9. concentrationthe mixture was concentrated under reduced pressure
  10. extractionThe residue was extracted with ethyl acetate
  11. washthe organic layer was washed with sodium hydrogen carbonate solution
  12. concentrationconcentrated
  13. customThe residue was purified with silica gel column chromatography

Sources & evidence

ORD record
ord-9c6dc37aef164d25a33f538e44685b0f
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

Loading…