Acetic Acid → N-[1-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-2-oxo-2-phenylethyl]acetamide

HRID 915005Notes

Reaction equation

HRID 915005 reaction equation
[CH:1]([N:4]1[C:9](=[O:10])[CH:8]=[CH:7][C:6]([C:11](=[N:20]O)[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:13])=[N:5]1)([CH3:3])[CH3:2].[C:22](OC(=O)C)(=[O:24])[CH3:23].CC(O)=O>CCOC(C)=O.[Zn]>[CH:1]([N:4]1[C:9](=[O:10])[CH:8]=[CH:7][C:6]([CH:11]([NH:20][C:22](=[O:24])[CH3:23])[C:12](=[O:13])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:5]1)([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 1363499311-(1-Isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-2-phenyl-1,2-ethanedione 1-oxime

Product 1

HCID 69333258N-[1-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-2-oxo-2-phenylethyl]acetamide

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Zinc dust (1.57 g) was added in portions to a suspension of 1-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-2-phenyl-1,2-ethanedione 1-oxime (856 mg) in a mixture acetic anhydride (1.7 ml) and AcOH (10 ml) under ambient temperature and the mixture was stirred at the same temperature for 4 hours. An insoluble material was filtered off and a filtrate was concentrated under reduced pressure to give a residue. The residue was dissolved in EtOAc, washed with sat. aq. NaHCO3 solution, dried over MgSO4 and subjected to column chromatography on silica gel eluting with a mixture of MeOH and EtOAc (2:98 v/v) to give N-[1-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-2-oxo-2-phenylethyl]acetamide as a solid (724 mg).

Workup

  1. filtrationAn insoluble material was filtered off
  2. concentrationa filtrate was concentrated under reduced pressure
  3. customto give a residue
  4. washwashed with sat. aq. NaHCO3 solution
  5. dry with materialdried over MgSO4
  6. additionsubjected to column chromatography on silica gel eluting with a mixture of MeOH and EtOAc (2:98 v/v)

Sources & evidence

ORD record
ord-a47ff4fed4aa4047b901311efbd7ad54
Source dataset
uspto-grants-2007_09
Patent number
US07265120B2

Reaction notes

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