Hydroxyamine hydrochloride → 6-Fluoro-benzofuran-3-one oxime

HRID 1928883Notes

Reaction equation

HRID 1928883 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=O)[CH2:7][O:8][C:4]=2[CH:3]=1.C([O-])(=O)C.[Na+].Cl.[NH2:18][OH:19]>C(O)C>[F:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[N:18][OH:19])[CH2:7][O:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 183543126-Fluoro-2,3-dihydro-1-benzofuran-3-one

Product 1

HCID 866341876-Fluoro-benzofuran-3-one oximeYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
23 °C

Procedure

A mixture of 6-fluoro-benzofuran-3-one (CAS 351528-80-8) (5.93 g, 39 mmol), sodium acetate (6.587 g, 80 mmol) and hydroxylamine hydrochloride (5.553 g, 80 mmol) in ethanol (70 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 white solid (5.19 g, 80%, HPLC 1.489 min); MS (ISN) m/e=168.1 [(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-1164b264e5ac461a8127294feabcb5b8
Source dataset
uspto-grants-2012_05
Patent number
US08183380B2

Reaction notes

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