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

HRID 1931523Notes

Reaction equation

HRID 1931523 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[C:9](=O)[CH2:10][O:11][C:7]=2[CH:6]=[CH:5][CH:4]=1.C([O-])(=O)C.[Na+].Cl.[NH2:19][OH:20]>C(O)C>[CH3:1][O:2][C:3]1[C:8]2[C:9](=[N:19][OH:20])[CH2:10][O:11][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 6391464-Methoxybenzofuran-3(2H)-one

Product 1

HCID 866341844-Methoxy-benzofuran-3-one oximeYield 174.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-methoxy-benzofuran-3-one (CAS 7169-35-9) (4.9 g, 19 mmol), sodium acetate (3.06 g, 38 mmol) and hydroxylamine hydrochloride (2.58 g, 38 mmol) in ethanol (40 ml) was refluxed for 6 h. Cooled to room temperature, filtered the precipitate off, washed with ethanol and dried in high vacuum to give 4-methoxy-benzofuran-3-one oxime as a white solid (5.93 g, 100%); MS: m/e=180.2 (M+H+).

Workup

  1. temperaturewas refluxed for 6 h
  2. filtrationfiltered the precipitate off,
  3. washwashed with ethanol
  4. customdried in high vacuum

Sources & evidence

ORD record
ord-96af7c5bcbd3411ebcde25d63c2397f0
Source dataset
uspto-grants-2012_05
Patent number
US08188284B2

Reaction notes

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