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

HRID 1695581Notes

Reaction equation

HRID 1695581 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 271.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
23 °C

Procedure

A mixture of 4-methoxy-benzofuran-3-one (CAS 7169-35-9) (30 g, 183 mmol; HPLC 1.241 min), sodium acetate (30.9 g, 375 mmol) and hydroxylamine hydrochloride (5.14 g, 57 mmol) in ethanol (310 ml) was refluxed for 4 h. Cooled to 23° C., filtered the precipitate off, washed with aqueous ethanol and dried in high vacuum to give the title compound as a light red solid (27.74 g, 88%; HPLC 1.448 min); MS (ISP) m/e=180.2 [(M+H)+].

Workup

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

Sources & evidence

ORD record
ord-c992812bcb944e168b2076045bc136d7
Source dataset
uspto-grants-2012_04
Patent number
US08163740B2

Reaction notes

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