Hydrochloric Acid → (E)-2-(Hydroxyimino)-N-methyl-2-(2-phenoxyphenyl)acetamide

HRID 1779718Notes

Reaction equation

HRID 1779718 reaction equation
[NH2:1][OH:2].[CH3:3][NH:4][C:5](=[O:21])[C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=O.Cl>C1(C)C=CC=CC=1>[CH3:3][NH:4][C:5](=[O:21])/[C:6](/[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[N:1]/[OH:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 11780091N-methyl-2-(2-phenoxyphenyl)-2-oxoacetamide

Product 1

HCID 9816878(E)-2-(Hydroxyimino)-N-methyl-2-(2-phenoxyphenyl)acetamideYield 98%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Toluene (20 ml) and a 50% aqueous solution (0.71 ml, 12 mmol) of hydroxylamine were added to N-methyl-2-(2-phenoxyphenyl)-2-oxoacetamide (2.55 g, 10 mmol). The mixture was heated under reflux for 4 hours (E/Z=40/60). After cooling, conc. hydrochloric acid (3.0 ml, 30 mmol) was added, and the mixture was stirred at room temperature for 24 hours. After completion of the reaction, the resulting crystals were separated by filtration, washed with water and toluene and dried to give (E)-N-methyl-2-(2-phenoxyphenyl)-2-hydroxyiminoacetamide (2.65 g, Yield: 98.0%, E/Z=98/2).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 4 hours (E/Z=40/60)
  3. temperatureAfter cooling
  4. customAfter completion of the reaction
  5. customthe resulting crystals were separated by filtration
  6. washwashed with water and toluene
  7. customdried

Sources & evidence

ORD record
ord-fdd44d3b36d647ef9d1b1bece258d373
Source dataset
uspto-grants-1997_05
Patent number
US05627284

Reaction notes

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