Acetic Anhydride → Ethyl 2-acetamido-3-oxobutanoate

HRID 1981637Notes

Reaction equation

HRID 1981637 reaction equation
[N:1](=[C:3]([C:9]([CH3:11])=[O:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5])O.[C:12](OC(=O)C)(=[O:14])[CH3:13].[H][H]>[Pd]>[C:12]([NH:1][CH:3]([C:9]([CH3:11])=[O:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5])(=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 178418361HCID 178418361, compoundHCID 178472877HCID 178472877, compound

Product 1

HCID 224840Ethyl 2-acetamido-3-oxobutanoateYield 92.3%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst2×

Procedure

A Parr flask was charged with 0.2 mol of ethyl 2-oximinoacetoacetate, 0.4 mol of acetic anhydride, 45 psi of hydrogen, and a mixture of 0.25 g of 5% palladium-on-carbon and 0.4 g of 10% palladium-on-carbon and shaken for about 22 hours. Work-up of the resultant reaction mixture provided a 92.3% yield of ethyl 2-acetamidoacetoacetate.

Workup

  1. customWork-up of the resultant reaction mixture

Sources & evidence

ORD record
ord-47f2e7cec1074d90a983d33959783130
Source dataset
uspto-grants-1986_06
Patent number
US04593118

Reaction notes

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