Hydroxylamine HCl → N-(2-phenylcyclohex-2-en-1-ylidene)hydroxylamine

HRID 1683734Notes

Reaction equation

HRID 1683734 reaction equation
[C:1]1([C:7]2[C:8](=O)[CH2:9][CH2:10][CH2:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].[OH:15][NH3+:16]>N1C=CC=CC=1>[C:1]1([C:7]2[C:8](=[N:16][OH:15])[CH2:9][CH2:10][CH2:11][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 21645Hydroxylamine HClHCID 12014012-Phenyl-2-cyclohexen-1-one

Product 1

HCID 604484N-(2-phenylcyclohex-2-en-1-ylidene)hydroxylamineYield 83.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 2-phenyl-2-cyclohexen-1-one (0.6 g, 3.5 mmol, Tetrahedron 1972, 28, 2369), hydroxylammonium chloride (0.5 g, 7 mmol) and dry pyridine (15 ml) was heated at reflux for 3 h. The reaction mixture was allowed to cool and the solvent was evaporated in vacuo. The residue was dissolved in a mixture of ethyl acetate and water. A 10% citric acid solution was added until acidic pH and the phases were separated. The organic phase was extracted with a 10% citric acid solution and dried (MgSO4). The solvent was evaporated in vacuo to give 0.55 g of 2-phenyl-2-cyclohexen-1 -one oxime. M.p. 144°-146° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 3 h
  3. temperatureto cool
  4. customthe solvent was evaporated in vacuo
  5. dissolutionThe residue was dissolved in a mixture of ethyl acetate and water
  6. additionA 10% citric acid solution was added until acidic pH
  7. customthe phases were separated
  8. extractionThe organic phase was extracted with a 10% citric acid solution
  9. dry with materialdried (MgSO4)
  10. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-9471297188524d38bc71adfdf7eabcfc
Source dataset
uspto-grants-1997_06
Patent number
US05639766

Reaction notes

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