Hydroxyamine hydrochloride → 4-Ethoxy-benzofuran-3-one oxime

HRID 1928866Notes

Reaction equation

HRID 1928866 reaction equation
[CH2:1]([O:3][C:4]1[C:9]2[C:10](=O)[CH2:11][O:12][C:8]=2[CH:7]=[CH:6][CH:5]=1)[CH3:2].C([O-])(=O)C.[Na+].Cl.[NH2:20][OH:21]>C(O)C.O>[CH2:1]([O:3][C:4]1[C:9]2[C:10](=[N:20][OH:21])[CH2:11][O:12][C:8]=2[CH:7]=[CH:6][CH:5]=1)[CH3:2]

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 686322724-Ethoxy-benzofuran-3-one

Product 1

HCID 866341864-Ethoxy-benzofuran-3-one oximeYield 93%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
23 °C

Procedure

A mixture of 4-ethoxy-benzofuran-3-one (CAS no: 7169-36-0) (4.18 g, 23.5 mmol), sodium acetate (3.96 g, 48.3 mmol) and hydroxylamine hydrochloride (3.34 g, 48.1 mmol) in ethanol (30 mL) was refluxed for 16 h. Cooled to 23° C., diluted with water (50 mL), filtered the precipitate off, washed with water, ethanol and diethyl ether and dried in high vacuum to give the title compound as a white solid (4.2 g, 93%); MS: m/e=194.3 (M+H+).

Workup

  1. temperaturewas refluxed for 16 h
  2. filtrationfiltered the precipitate off,
  3. washwashed with water, ethanol and diethyl ether
  4. customdried in high vacuum

Sources & evidence

ORD record
ord-f20a39b79b404aa2a5afa4ebd3b9998c
Source dataset
uspto-grants-2012_05
Patent number
US08183380B2

Reaction notes

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