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

HRID 750128Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[N:6]([NH:23][CH3:24])[C:7](=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([Cl:21])=[CH:10][CH:9]=2)=[O:4].[C:25](=O)([O-])[O-].[K+].[K+].CI>CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1[N:6]([N:23]([CH3:25])[CH3:24])[C:7](=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([Cl:21])=[CH:10][CH:9]=2)=[O:4]

Participants

Conditions

Temperature: 80 °C

Procedure

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.

Workup

concentrationThe reaction mixture was concentrated
additionethyl acetate was added to the obtained residue
washThe mixture was washed with water and brine
dry with materialdried over sodium sulfate
concentrationconcentrated
customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1)
customcrystallized from isopropyl ether

Sources & evidence

ORD record: ord-4151e229453642639bc4cb91592dd12f
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07402595B2

Reaction notes

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