Hydroxylamine HCl → N-(2-Phenyl-3,4-dihydronaphthalen-1(2H)-ylidene)hydroxylamine

HRID 1683740Notes

Reaction equation

HRID 1683740 reaction equation
[C:1]1([CH:7]2[CH2:16][CH2:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]2=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].[OH:19][NH3+:20]>N1C=CC=CC=1>[C:1]1([CH:7]2[CH2:16][CH2:15][C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]2=[N:20][OH:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 21645Hydroxylamine HClHCID 3483282-Phenyl-1-tetralone

Product 1

HCID 71357281N-(2-Phenyl-3,4-dihydronaphthalen-1(2H)-ylidene)hydroxylamineYield 101.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 2-phenyl-1-tetralone (1.1 g, 5 mmol, J. Am. Chem. Soc. 1949, 71, 1092), hydroxylammonium chloride (0.7 g, 10 mmol) and dry pyridine (30 ml) was heated at reflux for 4 h and then stirred at ambient temperature overnight. The solvent was evaporated in vacuo and the residue was stirred in a mixture of ethyl acetate (50 ml) and 10% citric acid (50 ml). The phases were separated and the organic phase was washed with water and dried (MgSO4). The solvent was evaporated in vacuo to give 1.2 g of 2-phenyl-1-tetralone oxime as a solid. M.p. 156°-157° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 h
  3. customThe solvent was evaporated in vacuo
  4. stirringthe residue was stirred in a mixture of ethyl acetate (50 ml) and 10% citric acid (50 ml)
  5. customThe phases were separated
  6. washthe organic phase was washed with water
  7. dry with materialdried (MgSO4)
  8. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-fda63738648c4021a97760be1fa57d27
Source dataset
uspto-grants-1997_06
Patent number
US05639766

Reaction notes

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