Acetic Anhydride → N-{4-[(E)-1-(5-Chloro-6-oxo-1,6-dihydropyridin-2-yl)-2-cyclopentylethenyl]phenyl}acetamide

Reaction equation

C(O[C:5](=[O:7])[CH3:6])(=O)C.[NH2:8][C:9]1[CH:14]=[CH:13][C:12](/[C:15](/[C:22]2[NH:27][C:26](=[O:28])[C:25]([Cl:29])=[CH:24][CH:23]=2)=[CH:16]\[CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)=[CH:11][CH:10]=1.C(=O)(O)[O-].[Na+]>>[Cl:29][C:25]1[C:26](=[O:28])[NH:27][C:22](/[C:15](/[C:12]2[CH:13]=[CH:14][C:9]([NH:8][C:5](=[O:7])[CH3:6])=[CH:10][CH:11]=2)=[CH:16]/[CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)=[CH:23][CH:24]=1

Participants

Reactant 3

HCID 7918Acetic Anhydride

HCID 516892Sodium Bicarbonate

HCID 674008996-[(E)-1-(4-aminophenyl)-2-cyclopentylethenyl]-3-chloropyridin-2(1H)-one

Product 1

HCID 67399264N-{4-[(E)-1-(5-Chloro-6-oxo-1,6-dihydropyridin-2-yl)-2-cyclopentylethenyl]phenyl}acetamideYield 38%

Procedure

Acetic anhydride (5 mL) was added to 6-[(E)-1-(4-aminophenyl)-2-cyclopentylethenyl]-3-chloropyridin-2(1H)-one (173 mg), and the mixture was stirred at room temperature for 15 minutes. Saturated aqueous sodium bicarbonate was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate. After filtration, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1→0:1). This was powdered with ethyl acetate, and filtration operation gave the title compound as a light yellow powder (75 mg, 38%).