Hydroxylamine → 7-Hydroxy-4-methyl-1-indanone oxime

HRID 414686Notes

Reaction equation

HRID 414686 reaction equation
Cl.[NH2:2][OH:3].C(=O)([O-])[O-].[K+].[K+].NO.[OH:12][C:13]1[CH:14]=[CH:15][C:16]([CH3:23])=[C:17]2[C:21]=1[C:20](=O)[CH2:19][CH2:18]2>CO.C(OCC)(=O)C>[OH:12][C:13]1[CH:14]=[CH:15][C:16]([CH3:23])=[C:17]2[C:21]=1[C:20](=[N:2][OH:3])[CH2:19][CH2:18]2

Participants

7

Reactant 4

HCID 787HydroxylamineHCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 124362447-Hydroxy-4-methyl-1-indanone

Product 1

HCID 1363428377-Hydroxy-4-methyl-1-indanone oxime

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

28 Grams of hydroxylamine hydrochloride and 56 g of potassium carbonate were added in 400 ml of methanol, and the mixture was refluxed by hetting for 30 minutes. After cooling the reaction mixture to a room temperature, the supernatant liquor was collected by separation to prepare a methanol solution of hydroxylamine. To this methanol solution of hydroxylamine was added 16.2 g of 7-hydroxy-4-methyl-1-indanone and refluxed by heating for 5 hours under stirring condition. The reaction mixture was concentrated to dryness under a reduced pressure. To the residue thus obtained was added 200 ml of ethyl acetate, then the insoluble matter was removed by filtration. The filtrate was concentrated to dryness under a reduced pressure, and the residue was recrystallized from methanol to obtain 17.6 g of 7-hydroxy-4-methyl-1-indanone oxime in the form of colorless needle-like crystals.

Workup

  1. temperaturethe mixture was refluxed
  2. customthe supernatant liquor was collected by separation
  3. customto prepare a methanol solution of hydroxylamine
  4. temperaturerefluxed
  5. temperatureby heating for 5 hours
  6. concentrationThe reaction mixture was concentrated to dryness under a reduced pressure
  7. customTo the residue thus obtained
  8. customthe insoluble matter was removed by filtration
  9. concentrationThe filtrate was concentrated to dryness under a reduced pressure
  10. customthe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-df6ed25f171a4a37b829838d7a2d98ed
Source dataset
uspto-grants-1988_12
Patent number
US04792628

Reaction notes

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