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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2229277Generated: October 31, 2026

Water → 6-(4-Chlorobenzoyl)-4-(3-methoxyphenyl)-1-methyl-2(1h)-quinolinone

https://huagongshe.com/reaction/2229277

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantMethyl iodideHCID 6328—
Reactant6-(4-Chlorobenzoyl)-4-(3-methoxyphenyl)-2(1h)-quinolinoneHCID 22714370—
CatalystBenzyl triethylammonium chlorideHCID 66133—
SolventTetrahydrofuranHCID 8028—
SolventSodium HydroxideHCID 14798—
Product6-(4-Chlorobenzoyl)-4-(3-methoxyphenyl)-1-methyl-2(1h)-quinolinoneHCID 2271435790%

Reaction Steps

Methyl iodide (1.58 ml) was added to a solution of interm. (5-f) (7.6 g) and benzyltriethylammonium chloride (BTEAC) (2.23 g) in THF (80 ml) and sodium hydroxide (40%, 80 ml). The mixture was stirred at room temperature for 2 hours. Water was added and the mixture was extracted with ethyl acetate. The organic layer was dried (MgSO4), filtered, and the solvent was evaporated. The residue was purified by flash column chromatography over silica gel (eluent: DCM 100%). The desired fractions were collected and the solvent was evaporated, yielding 7.1g (90%) of 6-(4-chlorobenzoyl)-4-(3-methoxyphenyl)-1-methyl-2(1H)-quinolinone (interm. 5-g).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06420387B1
Source datasetuspto-grants-2002_07
ORD IDord-1273c7c5b1f44f968503912192f09300
Source noteuspto-grants-2002_07