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

HRID 70609Notes

Reaction equation

HRID 70609 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

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 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%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationAfter filtration
  5. customthe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1→0:1)
  7. filtrationThis was powdered with ethyl acetate, and filtration operation

Sources & evidence

ORD record
ord-d520d21861fa4623b53270a7bb516f6f
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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