Sulfuric Acid → 2-hydroxyimino-N-phenylacetamide

HRID 488790

Reaction equation

HRID 488790 reaction equation
[C:1]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:6])[CH2:2]C(C)=O.[N:14]([O-])=[O:15].[Na+].S(=O)(=O)(O)O>[OH-].[Na+]>[OH:15][N:14]=[CH:2][C:1]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:6]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 7592AcetoacetanilideHCID 23668193Sodium Nitrite

Product 1

HCID 63990632-hydroxyimino-N-phenylacetamideYield 98.5%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

Acetoacetanilide (25.0 g, 0.14 mol) and sodium nitrite (12.65 g, 0.18 mol) were dissolved in aqueous sodium hydroxide solution (140 ml, 1 N) and the resulting solution was added dropwise over 20 min to an aqueous solution of sulfuric acid (120 ml conc. H2SO4 in 950 ml water) cooled in an ice bath. The reaction mixture was stirred at 0° C. for 30 min, then the precipitate was filtered and washed with water to yield 2-hydroxyiminoacetanilide (22.64 g., 78% yield) as a pale yellow solid.

Workup

  1. temperaturecooled in an ice bath
  2. filtrationthe precipitate was filtered
  3. washwashed with water

Sources & evidence

ORD record
ord-abc6f84208b84ffcba07207732b9c7ba
Source dataset
uspto-grants-2005_12
Patent number
US06974813B2

Linked notes

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