Hydroxyamine hydrochloride → 5,7-Dimethyl-8-hydroxy-1,2,3,4,4a,9a-hexahydro-9-fluorenone oxime

HRID 2051426Notes

Reaction equation

HRID 2051426 reaction equation
Cl.[NH2:2][OH:3].[CH3:4][C:5]1[CH:17]=[C:16]([CH3:18])[C:15]([OH:19])=[C:14]2[C:6]=1[CH:7]1[CH:12]([C:13]2=O)[CH2:11][CH2:10][CH2:9][CH2:8]1>N1C=CC=CC=1>[CH3:4][C:5]1[CH:17]=[C:16]([CH3:18])[C:15]([OH:19])=[C:14]2[C:6]=1[CH:7]1[CH:12]([C:13]2=[N:2][OH:3])[CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 151571835,7-Dimethyl-8-hydroxy-1,2,3,4,4a,9a-hexahydro-9-fluorenone

Product 1

HCID 1363411795,7-Dimethyl-8-hydroxy-1,2,3,4,4a,9a-hexahydro-9-fluorenone oxime

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

7.99 Grams of hydroxylamine hydrochloride was added to a solution prepared by dissolving 17.22 g of 5,7-dimethyl-8-hydroxy-1,2,3,4,4a,9a-hexahydro-9-fluorenone in 100 ml of pyridine and the mixture was refluxed under heating for 2 hours. Pyridine was distilled off under reduced pressure and the resulting residue was extracted with 300 ml of chloroform. The extract was washed with water 1% hydrochloric acid and then with saturated aqueous sodium chloride solution and then dried with anhydrous magnesium sulfate. After the solvent was distilled off, the product was recrystallized from ethanol to obtain 11.56 g of 5,7-dimethyl-8-hydroxy-1,2,3,4,4a,9a-hexahydro-9-fluorenone oxime as a mixture of syn-isomer and anti-isomer.

Workup

  1. customprepared
  2. temperaturethe mixture was refluxed
  3. temperatureunder heating for 2 hours
  4. distillationPyridine was distilled off under reduced pressure
  5. extractionthe resulting residue was extracted with 300 ml of chloroform
  6. washThe extract was washed with water 1% hydrochloric acid
  7. dry with materialwith saturated aqueous sodium chloride solution and then dried with anhydrous magnesium sulfate
  8. distillationAfter the solvent was distilled off
  9. customthe product was recrystallized from ethanol

Sources & evidence

ORD record
ord-1a708f3666034e64bbe548a4cc770e5f
Source dataset
uspto-grants-1991_05
Patent number
US05017724

Reaction notes

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