1-Indanone → 2,3-Dihydro-1H-inden-1-one oxime

HRID 1657184Notes

Reaction equation

HRID 1657184 reaction equation
[C:1]1(=O)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.Cl.[NH2:12][OH:13]>CO.N1C=CC=CC=1>[C:1]1(=[N:12][OH:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 67351-IndanoneHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 3023232,3-Dihydro-1H-inden-1-one oximeYield 93%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1049PyridineSolvent

Procedure

1-Indanone (4.00 g, 30.3 mmol) and hydroxylamine hydrochloride (5.26 g, 75.7 mmol) were dissolved in a mixture of methanol (40 ml) and pyridine (10 ml) and stirred for 3 hours at ambient temperature. The reaction mixture was concentrated in vacuo and the resultant residue was diluted with 1N HCl (100 ml) and extracted three times with methylene chloride. The organic layer was dried over MgSO4 and concentrated in vacuo to provide 4.13 g (93% yield) of the desired 1-indanone oxime as white needles.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionthe resultant residue was diluted with 1N HCl (100 ml)
  3. extractionextracted three times with methylene chloride
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-34268baac8a849e8acd2a55dcc74455f
Source dataset
uspto-grants-1993_10
Patent number
US05256789

Reaction notes

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