Hydroxylamine, sulfate (1:1) → (E)-2-(Hydroxyimino)-N-methyl-2-(2-phenoxyphenyl)acetamide

HRID 1779717Notes

Reaction equation

HRID 1779717 reaction equation
[CH3:1][NH:2][C:3](=[O:19])[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=O.S(O)(O)(=O)=O.[NH2:25][OH:26]>CO>[CH3:1][NH:2][C:3](=[O:19])/[C:4](/[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[N:25]/[OH:26]

Participants

4

Reactant 2

HCID 159255Hydroxylamine, sulfate (1:1)HCID 11780091N-methyl-2-(2-phenoxyphenyl)-2-oxoacetamide

Product 1

HCID 9816878(E)-2-(Hydroxyimino)-N-methyl-2-(2-phenoxyphenyl)acetamideYield 95.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

N-Methyl-2-(2-phenoxyphenyl)-2-oxoacetamide (2.55 g, 10 mmol) was dissolved in methyl alcohol (10 ml). Hydroxylamine sulfate (0.99 g, 12 mmol) was added, followed by heating under reflux for 3 hours. After completion of the reaction, methyl alcohol was evaporated under reduced pressure. Toluene (10 ml) and conc. hydrochloric acid (1.04 g) were added to the resulting residue (E/Z=41/59), and the mixture was stirred at room temperature for 20.5 hours. After completion of the reaction, water (300 ml) was added. The mixture was extracted with ethyl acetate (300 ml), washed with brine twice, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give (E)-N-methyl-2-(2-phenoxyphenyl)-2-hydroxyiminoacetamide (2.58 g, Yield: 95.6%, E/Z=96/4).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 3 hours
  3. customwas evaporated under reduced pressure
  4. additionToluene (10 ml) and conc. hydrochloric acid (1.04 g) were added to the resulting residue (E/Z=41/59)
  5. customAfter completion of the reaction, water (300 ml)
  6. additionwas added
  7. extractionThe mixture was extracted with ethyl acetate (300 ml)
  8. washwashed with brine twice
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1e55cc9d76874cbaa8333280d737bb16
Source dataset
uspto-grants-1997_05
Patent number
US05627284

Reaction notes

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