Hydroxylamine HCl → HCID 73455956, compound

HRID 1636020Notes

Reaction equation

HRID 1636020 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][CH3:14])[CH:6]=1)=O.[Cl-].[OH:18][NH3+:19].C([O-])(=O)C.[Na+]>C(O)C.O>[F:1][C:2]([F:16])([F:15])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[C:7]([O:13][CH3:14])[CH:6]=1)=[N:19][OH:18]

Participants

6

Reactant 3

HCID 21645Hydroxylamine HClHCID 517045Sodium AcetateHCID 27584933',4'-Dimethoxy-2,2,2-trifluoroacetophenone

Product 1

HCID 73455956HCID 73455956, compoundYield 95.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

2.9 g (9.7 mmol) of 2,2,2-trifluoro-1-(3,4-dimethoxyphenyl)-ethanone are dissolved in 12 ml of ethanol at 80° C. To the solution are added dropwise 0.83 g (12.0 mmol) of hydroxylammonium chloride and 1.2 g (15.0 mmol) of sodium acetate dissolved in 6 ml of water. The reaction mixture is refluxed for 7.5 hours, poured into ice water, and extracted with ether. The organic phase is washed with water and brine, dried over MgSO4, and concentrated, yielding 2.3 g of 2,2,2-trifluoro-1-(3,4-dimethoxyphenyl)-ethanone oxime. The crude product is used in the next reaction step without further purification.

Workup

  1. temperatureThe reaction mixture is refluxed for 7.5 hours
  2. extractionextracted with ether
  3. washThe organic phase is washed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-388b49e9ec0444ddb2708ebc37e73051
Source dataset
uspto-grants-2003_01
Patent number
US06512020B1

Reaction notes

Loading…