Hydroxylamine HCl → 3-Phenyl-1-indanone oxime

HRID 1683743Notes

Reaction equation

HRID 1683743 reaction equation
[C:1]1([CH:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=O)[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].[OH:18][NH3+:19]>N1C=CC=CC=1>[C:1]1([CH:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=[N:19][OH:18])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 21645Hydroxylamine HClHCID 981461-Indanone, 3-phenyl-

Product 1

HCID 731839393-Phenyl-1-indanone oximeYield 62.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 3-phenyl-1-indanone (4.2 g, 20 mmol, J. Chem. Soc. 1949, 2957), hydroxylammonium chloride (2.8 g, 40 mmol) and pyridine (30 ml) was heated at reflux overnight. The reaction mixture was allowed to cool and the solvent was evaporated in vacuo. The residue was dissolved in ethyl acetate and washed with excess 10% citric acid solution. The organic phase was dried (MgSO4) and the solvent evaporated in vacuo to give a solid which was triturated with a mixture of cyclohexane and ethyl acetate. The solid was isolated by filtration and dried in air to give 2.8 g of 3-phenyl-1-indanone oxime as a solid. M.p. 123°-125° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. temperatureto cool
  4. customthe solvent was evaporated in vacuo
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed with excess 10% citric acid solution
  7. dry with materialThe organic phase was dried (MgSO4)
  8. customthe solvent evaporated in vacuo
  9. customto give a solid which
  10. customwas triturated with a mixture of cyclohexane and ethyl acetate
  11. customThe solid was isolated by filtration
  12. customdried in air

Sources & evidence

ORD record
ord-5a1a6083e0204ac3a177a4e1dc07867e
Source dataset
uspto-grants-1997_06
Patent number
US05639766

Reaction notes

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