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

HRID 1756742Notes

Reaction equation

HRID 1756742 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-3bd77effff06463a86bad3004dca5749
Source dataset
uspto-grants-1995_08
Patent number
US05442063

Reaction notes

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