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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2298980Generated: October 30, 2026

Acetic Anhydride → 6-(4-Chloro-benzoyl)-4-(3-iodo-phenyl)-1H-quinolin-2-one

https://huagongshe.com/reaction/2298980

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAcetic AnhydrideHCID 7918—
ReactantTriethylamineHCID 8471—
Reactant[6-Amino-3-(4-chloro-benzoyl)-cyclohexa-2,4-dienyl]-(3-iodo-phenyl)-methanoneHCID 15489628—
Catalyst4-(Dimethylamino)pyridineHCID 14284—
SolventTolueneHCID 1140—
Product6-(4-Chloro-benzoyl)-4-(3-iodo-phenyl)-1H-quinolin-2-oneHCID 15489629—

Reaction Steps

[6-Amino-3-(4-chloro-benzoyl)-cyclohexa-2,4-dienyl]-(3-iodo-phenyl)-methan-one (60 g, 130 mMol) was dissolved in anhydrous toluene (450 mL) under an atmosphere of dry N2. To this solution was added 180 mL of triethylamine (NEt3), 50 mL of acetic anhydride (Ac2O) and 1.60 g (13.0 mMol) of 4-dimethylaminopyridine (DMAP). The reaction mixture was then heated to reflux and stirred at this temperature for 20 hours. The reaction mixture was cooled to ambient temperature and the precipitate was collected via suction filtration. The solid was washed with ethyl ether (Et2O) and dried under vacuum to give of the titled compound (63 g) which was used without further purification.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06495564B1
Source datasetuspto-grants-2002_12
ORD IDord-be9b192ef10f408793ae4c57ab254bd9
Source noteuspto-grants-2002_12