Hydroxyamine hydrochloride → 1-(3,4-Difluorophenyl)-2-hydroxy-propan-1-one-oxime

HRID 2187550Notes

Reaction equation

HRID 2187550 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9](=O)[CH:10]([OH:12])[CH3:11])[CH:5]=[CH:6][C:7]=1[F:8].Cl.[NH2:15][OH:16].C([O-])(=O)C.[Na+]>CO>[F:1][C:2]1[CH:3]=[C:4]([C:9](=[N:15][OH:16])[CH:10]([OH:12])[CH3:11])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 229935141-(3,4-Difluorophenyl)-2-hydroxy-propan-1-one

Product 1

HCID 740145381-(3,4-Difluorophenyl)-2-hydroxy-propan-1-one-oximeYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a well stirred solution of 1-(3,4-difluorophenyl)-2-hydroxy-propan-1-one (5.5 g, 29.6 mmol) in MeOH (200 mL) was added hydroxylamine hydrochloride (2.6 g, 38.4 mmol) and sodium acetate (8.1 g, 59.2 mmol) and the turbid solution was stirred overnight at room temperature. The solvent was evaporated and the residue was extracted with CH2Cl2. The organic layer was washed with sat. NaHCO3, separated, dried over NaSO4 and then filtered. The solvent was removed in vacuo to obtain 1-(3,4-Difluorophenyl)-2-hydroxy-propan-1-one-oxime as an orangish yellow oil (5.3 g, 97%). It was used in the next step without purification.

Workup

  1. customThe solvent was evaporated
  2. extractionthe residue was extracted with CH2Cl2
  3. washThe organic layer was washed with sat. NaHCO3
  4. customseparated
  5. dry with materialdried over NaSO4
  6. filtrationfiltered
  7. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-f3325224e2174a03b024c8000995e25b
Source dataset
uspto-grants-2002_06
Patent number
US06410554B1

Reaction notes

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