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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1700642Generated: November 1, 2026

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

https://huagongshe.com/reaction/1700642

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium IodideHCID 5238—
ReactantChloroacetoneHCID 6571—
ReactantPotassium CarbonateHCID 11430—
Reactant5-(2-Chlorophenyl)-1-[2-(4-methylphenylsulfonyl)hydrazino]cyclohexen-3-oneHCID 11728881—
SolventEthanolHCID 702—
Solvent1,2-DimethoxyethaneHCID 8071—
Product4-Methyl-7-(2-chlorophenyl)-5,6,7,8-tetrahydrocinnolin-5-oneHCID 1104392641.6%

Reaction Conditions

Temperature80 °C

Reaction Steps

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.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06350749B1
Source datasetuspto-grants-2002_02
ORD IDord-269d9bb809e4452f9ed42ebee633a72f
Source noteuspto-grants-2002_02