Methanol → HCID 73604849, compound

HRID 1637002Notes

Reaction equation

HRID 1637002 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12](=O)[C:13]([NH2:15])=[O:14])(=[O:3])[CH3:2].Cl.[NH2:18][OH:19].C([O-])(=O)C.[K+].CO>O>[C:1]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12](=[N:18][OH:19])[C:13]([NH2:15])=[O:14])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 443297Hydroxyamine hydrochlorideHCID 517044Potassium AcetateHCID 19350201HCID 19350201, compound

Product 1

HCID 73604849HCID 73604849, compoundYield 70.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-(2-acetoxymethylphenyl)-2-oxoacetamide (1.56 g), 95% hydroxylamine hydrochloride (0.62 g), potassium acetate (1.34 g) and methanol (14 ml) was heated under reflux with stirring for 18 hours. After the mixture was cooled by allowing it to stand, water (about 150 ml) was added to the reaction mixture, and the mixture was extracted with ethyl acetate three times. The combined ethyl acetate layer was washed with saturated brine and dried over anhydrous sodium sulfate. Evaporation of the solvent under reduced pressure gave the crude product (1.55 g). The crude product was purified by column chromatography on silica gel (ethyl acetate:hexane=2:1) to give the title compound (1.18 g, yield: 70.9%) as a mixture of the E- and Z-isomers (E:Z=65:35 determined by 1H-NMR analysis).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. temperatureAfter the mixture was cooled
  4. extractionthe mixture was extracted with ethyl acetate three times
  5. washThe combined ethyl acetate layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customEvaporation of the solvent under reduced pressure
  8. customgave the crude product (1.55 g)
  9. customThe crude product was purified by column chromatography on silica gel (ethyl acetate:hexane=2:1)

Sources & evidence

ORD record
ord-c4af9ab050704014b3d5f13cfc9857a9
Source dataset
uspto-grants-2000_03
Patent number
US06037495

Reaction notes

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