7-Methoxy-1-indanone → 7-Methoxyindan-1-one oxime

HRID 1188705Notes

Reaction equation

HRID 1188705 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[C:10](=O)[CH2:9][CH2:8]2.Cl.[NH2:14][OH:15].C([O-])(=O)C.[Na+]>C(O)C.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:11]=1[C:10](=[N:14][OH:15])[CH2:9][CH2:8]2

Participants

6

Reactant 3

HCID 2881437-Methoxy-1-indanoneHCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium Acetate

Product 1

HCID 5949007-Methoxyindan-1-one oximeYield 100%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 7-methoxyindanone (5.0 g, 31 mmol) and hydroxylamine hydrochloride (12.9 g, 185 mmol) in 100 mL ethanol was added the solution of sodium acetate (11.4 g, 139 mmol) in 35 mL water at room temperature. The reaction mixture was heated at reflux for 4 h, then stirred at room temperature for 18 h. The suspension was filtered, the white solid was washed with water, ethanol and diethyl ether to give the title compound (5.4 g, 31 mmol, 98%). ESMS m/z 178 (M+H)+.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 4 h
  3. filtrationThe suspension was filtered
  4. washthe white solid was washed with water, ethanol and diethyl ether

Sources & evidence

ORD record
ord-8d25d3e094184f44a32e7354f8892b81
Source dataset
uspto-grants-2014_03
Patent number
US08674095B2

Reaction notes

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