Sulfuric Acid → 2-hydroxyimino-N-phenylacetamide

HRID 2298014

Reaction equation

HRID 2298014 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-c916ce4de7414023bfc41ad8ba0d765e
Source dataset
uspto-grants-2002_12
Patent number
US06492401B1

Linked notes

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