Water → N-[2-(2,6-dimethoxyquinolin-4-yl)ethyl]acetamide

HRID 725890Notes

Reaction equation

Cl[C:2]1[CH:11]=[C:10]([CH2:12][CH2:13][NH:14][C:15](=[O:17])[CH3:16])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:18][CH3:19])[CH:8]=2)[N:3]=1.[CH3:20][O-:21].[Na+].O>CO>[CH3:20][O:21][C:2]1[CH:11]=[C:10]([CH2:12][CH2:13][NH:14][C:15](=[O:17])[CH3:16])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:18][CH3:19])[CH:8]=2)[N:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of N-[2-(2-chloro-6-methoxyquinolin-4-yl)ethyl]acetamide (0.9 g, 3.2 mmol) and sodium methoxide (30 g, 28% methanol solution) in methanol (20 ml) was stirred at 60° C. overnight. The reaction mixture was poured into water, and the organic layer was extracted with ethyl acetate. The extract was washed with saturated brine and water and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The resulting residue was purified by column chromatography on silica gel (ethyl acetate) and recrystallized from a mixed solvent of ethyl acetate and hexane to obtain the title compound (0.46 g, 52%).

Workup

extractionthe organic layer was extracted with ethyl acetate
washThe extract was washed with saturated brine and water
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure
customThe resulting residue was purified by column chromatography on silica gel (ethyl acetate)
customrecrystallized from a mixed solvent of ethyl acetate and hexane

Sources & evidence

ORD record: ord-a090178fb9ce4ddb909b86eefa7e77e7
Source dataset: uspto-grants-1998_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05708005

Reaction notes

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