Sodium Iodide → 4-Methyl-7-(2-chlorophenyl)-5,6,7,8-tetrahydrocinnolin-5-one

HRID 1700642Notes

Reaction equation

HRID 1700642 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+].Cl[CH2:34][C:35](=O)[CH3:36].[I-].[Na+]>COCCOC.C(O)C>[CH3:36][C:35]1[C:11]2[C:10](=[O:26])[CH2:9][CH:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[CH2:13][C:12]=2[N:14]=[N:15][CH:34]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 117288815-(2-Chlorophenyl)-1-[2-(4-methylphenylsulfonyl)hydrazino]cyclohexen-3-one

Product 1

HCID 110439264-Methyl-7-(2-chlorophenyl)-5,6,7,8-tetrahydrocinnolin-5-oneYield 41.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-(2-chlorophenyl)-1-[2-(4-methylphenylsulfonyl)hydrazino]cyclohexen-3-one (1.17 g), anhydrous potassium carbonate (1.1 g), chloroacetone (0.335 g), sodium iodide (0.4 g), ethanol (7.5 ml) and 1,2-dimethoxyethane (7.5 ml) was stirred at 80° C. for 4 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 4-methyl-7-(2-chlorophenyl)-5,6,7,8-tetrahydrocinnolin-5-one (0.34 g) as pale yellow crystals.

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-269d9bb809e4452f9ed42ebee633a72f
Source dataset
uspto-grants-2002_02
Patent number
US06350749B1

Reaction notes

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