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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 750128Generated: October 30, 2026

Methyl iodide → 6-chloro-2-dimethylamino-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl Ester

https://huagongshe.com/reaction/750128

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethyl iodideHCID 6328—
ReactantPotassium CarbonateHCID 11430—
Reactant6-chloro-2-methylamino-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl EsterHCID 10125945—
SolventDimethylformamideHCID 6228—
Product6-chloro-2-dimethylamino-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl EsterHCID 1028690156.3%

Reaction Conditions

Temperature80 °C

Reaction Steps

A mixture of 6-chloro-2-methylamino-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid methyl ester (800 mg), potassium carbonate (400 mg), methyl iodide (20 ml) and DMF (20 ml) was stirred at 80° C. for 3 days. The reaction mixture was concentrated, and ethyl acetate was added to the obtained residue. The mixture was washed with water and brine, dried over sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1) and crystallized from isopropyl ether to give the title compound (469 mg) as colorless crystals.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07402595B2
Source datasetuspto-grants-2008_07
ORD IDord-4151e229453642639bc4cb91592dd12f
Source noteuspto-grants-2008_07