Hydroxyamine hydrochloride → HCID 73504074, compound

HRID 971869Notes

Reaction equation

HRID 971869 reaction equation
O=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=[O:17])=[CH:11][CH:10]=1.Cl.[NH2:20][OH:21].C([O-])(=O)C.[Na+]>C(O)C>[OH:21][N:20]=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([OH:18])=[O:17])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 12799531HCID 12799531, compound

Product 1

HCID 73504074HCID 73504074, compoundYield 103.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 0.64 g of 4-(2-oxocyclohexan-1-ylmethyl)phenylacetic acid, 0.19 g of hydroxylamine hydrochloride, and 0.45 g of anhydrous sodium acetate in 10 ml of 80% ethanol was heated under reflux for 2 hours. The solvent was removed by distillation, water and ethyl acetate were added to the residue, the mixture was acidified by addition of diluted hydrochloric acid, the ethyl acetate layer separated and the water layer was then extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate, the solvent removed by distillation to give 0.7 g of the desired compound, which by recrystallization from ethyl acetate afforded colorless crystals, m.p. 180°-184° C.

Workup

  1. temperatureunder reflux for 2 hours
  2. customThe solvent was removed by distillation, water and ethyl acetate
  3. additionwere added to the residue
  4. additionthe mixture was acidified by addition of diluted hydrochloric acid
  5. customthe ethyl acetate layer separated
  6. extractionthe water layer was then extracted with ethyl acetate
  7. washThe extract was washed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. customthe solvent removed by distillation

Sources & evidence

ORD record
ord-b473126a78ee447fb886c74ac1822e60
Source dataset
uspto-grants-1979_07
Patent number
US04161538

Reaction notes

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