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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 351784Generated: October 30, 2026

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

https://huagongshe.com/reaction/351784

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, 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 7.1 g (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 numberUS06743805B2
Source datasetuspto-grants-2004_06
ORD IDord-37fd885100a242729146a6e71fd1eed8
Source noteuspto-grants-2004_06