Hydroxyamine hydrochloride → 2-(1H-indene-1-yl)acetaldoxime

HRID 1534795Notes

Reaction equation

HRID 1534795 reaction equation
[CH:1]1([CH2:10][CH:11]=O)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.Cl.[NH2:14][OH:15].C([O-])(=O)C.[Na+]>CO>[CH:1]1([CH2:10][CH:11]=[N:14][OH:15])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 19908307(1H-Inden-1-yl)acetaldehyde

Product 1

HCID 856179012-(1H-indene-1-yl)acetaldoxime

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(1H-indene-1-yl)acetaldehyde (1.5 g, 9.5 mmol), hydroxylamine hydrochloride (836 mg, 12.0 mmol), and sodium acetate (1.04 g, 12.7 mmol) were combined in methanol (50 ml) and stirred at ambient temperature overnight. The mixture was evaporated to dryness in vacuo and the residue treated with water and extracted with ether. The ether layer was washed with water, dried over sodium sulfate, filtered, and evaporated to dryness in vacuo. The residue was chromatographed on a silica gel coulmn eluted with 15% EtOAc in hexane followed by 22% EtOAc in hexane. The product fraction was evaporated to dryness in vacuo to provide 2-(1H-indene-1-yl)acetaldoxime.

Workup

  1. customThe mixture was evaporated to dryness in vacuo
  2. additionthe residue treated with water
  3. extractionextracted with ether
  4. washThe ether layer was washed with water
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness in vacuo
  8. customThe residue was chromatographed on a silica gel
  9. washcoulmn eluted with 15% EtOAc in hexane
  10. customThe product fraction was evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-0af7707961c5422aa9463e46a4c489fc
Source dataset
uspto-grants-1992_02
Patent number
US05091387

Reaction notes

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