Water → 2-(2-Phenoxyphenyl)-2-methoxyiminoacetamide

HRID 1078475Notes

Reaction equation

HRID 1078475 reaction equation
CO[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.Cl.[CH3:21][O:22][NH2:23].O.[OH-].[NH4+:26]>CO>[O:12]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[C:4](=[N:23][O:22][CH3:21])[C:3]([NH2:26])=[O:19])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14923Ammonium HydroxideHCID 521874O-Methylhydroxylamine hydrochlorideHCID 13729870Methyl 2-phenoxybenzoylformate

Product 1

HCID 539671372-(2-Phenoxyphenyl)-2-methoxyiminoacetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl-(2-phenoxyphenyl)-2-oxoacetate (0.70 g) in methanol (10 ml), 28% aqueous ammonium hydroxide (2.0 ml) was added, and the resultant mixture was stirred overnight, followed by removal of the solvent under reduced pressure. The residue was combined with diethyl ether (150 ml) and water (50 ml) under stirring and, upon dissolution, allowed to stand. The organic layer was separated, washed and dried over anhydrous sodium sulfate. Upon filtration, the filtrate was concentrated under reduced pressure to give residual yellow crystals, which were combined with methahol (10 ml) and O-methylhydroxylamine hydrochloride (1.49 g) while stirring and refluxed for 6 hours. Water (50 ml) was added to the reaction mixture, which was extracted with diethyl ether. The organic layer was washed with water and dried over anhydrous sodium sulfate, followed by filtration. The filtrate was concentrated under reduced pressure to give oily residue. The residue was purified by silica gel column chromatography with benzene to give 0.36 g of the objective compound. nD23.3 1.5978.

Workup

  1. customfollowed by removal of the solvent under reduced pressure
  2. customThe organic layer was separated
  3. washwashed
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationUpon filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customto give residual yellow crystals, which
  8. stirringwhile stirring
  9. temperaturerefluxed for 6 hours
  10. extractionwas extracted with diethyl ether
  11. washThe organic layer was washed with water
  12. dry with materialdried over anhydrous sodium sulfate
  13. filtrationfollowed by filtration
  14. concentrationThe filtrate was concentrated under reduced pressure
  15. customto give oily residue
  16. customThe residue was purified by silica gel column chromatography with benzene

Sources & evidence

ORD record
ord-d828b7956e3840b88e5ceeda1d56b9de
Source dataset
uspto-grants-1996_08
Patent number
US05548078

Reaction notes

Loading…