Acetic Acid → HCID 54437877, compound

HRID 1065500Notes

Reaction equation

HRID 1065500 reaction equation
O[N:2]=[C:3]([C:15](=[O:17])[CH3:16])[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)=[O:5].O.[C:19](O)(=[O:21])[CH3:20]>C(OC(=O)C)(=O)C.[Zn]>[C:19]([NH:2][CH:3]([C:15](=[O:17])[CH3:16])[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)=[O:5])(=[O:21])[CH3:20]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 178492393HCID 178492393, compound

Product 1

HCID 54437877HCID 54437877, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 7918Acetic AnhydrideSolvent

Procedure

To a stirred solution of 11.8 g of 2-(hydroxyimino)-N-(4-methoxyphenyl)-3-oxobutanamide in 30 ml of acetic acid and 10 ml of acetic anhydride at 20°-30° C. is added 10 g of zinc dust and the mixture is stirred for 1 hour. Water (150 ml) is added, the mixture is stirred for 2 hours, and the zinc is removed by filtration. The solvent is evaporated from the filtrate under reduced pressure and the resulting residue is recrystallized from methanol to give 2-acetylamino-N-(4-methoxyphenyl)-3-oxobutanamide.

Workup

  1. stirringthe mixture is stirred for 2 hours
  2. customthe zinc is removed by filtration
  3. customThe solvent is evaporated from the filtrate under reduced pressure
  4. customthe resulting residue is recrystallized from methanol

Sources & evidence

ORD record
ord-7d18119b398045b394ace8798774d20a
Source dataset
uspto-grants-1982_05
Patent number
US04329470

Reaction notes

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