2-Methylindanone → Methylindan-1-one oxime

HRID 1641377

Reaction equation

HRID 1641377 reaction equation
[CH3:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=O.Cl.[NH2:13][OH:14].C([O-])(=O)C.[Na+]>C(O)C.O>[CH3:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=[N:13][OH:14]

Participants

6

Reactant 3

HCID 2492622-MethylindanoneHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 73454082Methylindan-1-one oximeYield 89.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2-methyl-1-indanone (10 g, 0.0684 mol) and hydroxylamine hydrochloride (9.5 g, 0.1368 mol) in ethanol was stirred at 60° C., and a solution of sodium acetate (16.8 g, 0.2052 mol) in water added. The resulting mixture was then heated at reflux for 90 minutes, then cooled and the solid filtered. The crude product was washed with water and filtered to give 2-methyl-indan-1-one oxime (9.9 g, yield 81%), mp. 82-91° C., in 90% purity.

Workup

  1. temperatureThe resulting mixture was then heated
  2. temperatureat reflux for 90 minutes
  3. temperaturecooled
  4. filtrationthe solid filtered
  5. washThe crude product was washed with water
  6. filtrationfiltered

Sources & evidence

ORD record
ord-bc3dafd1fd074be09964f9c4bf057cae
Source dataset
uspto-grants-2012_02
Patent number
US08114991B2

Linked notes

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