Hydroxyamine hydrochloride → HCID 59339521, compound

HRID 12598Notes

Reaction equation

HRID 12598 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[CH2:10][CH2:11][CH3:12])=[CH:5][CH:4]=1.Cl.[NH2:17]O>C(O)C>[F:1][C:2]([F:15])([F:14])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]([NH2:17])[CH2:10][CH2:11][CH3:12])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 113789211-Butanone, 1-[4-(trifluoromethyl)phenyl]-

Product 1

HCID 59339521HCID 59339521, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-[4-(trifluoromethyl)phenyl]butan-1-one (6 g, 27.8 mmol) in ethanol (60 ml) was added hydroxylamine hydrochloride (5.79 g, 83.3 mmol) and the reaction heated to reflux and stirred for 16 h. The reaction was allowed to cool to room temperature and then concentrated in vacuo. The residue was taken up in ethyl acetate, washed twice with water, dried over sodium sulfate and concentrated in vacuo. The crude oxime was then dissolved in ethanol (100 ml) and Raney nickel (approx 1 g) added. The reaction was stirred under a balloon of hydrogen for 72 h. The reaction was filtered though celite (washing with ethanol) concentrated in vacuo, adsorbed onto silica gel and purified by flash column (50-80% ethyl acetate in hexanes) to yield the title compound (5 g, 83%) as colourless crystals.

Workup

  1. temperaturethe reaction heated
  2. temperatureto reflux
  3. concentrationconcentrated in vacuo
  4. washwashed twice with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. dissolutionThe crude oxime was then dissolved in ethanol (100 ml)
  8. additionRaney nickel (approx 1 g) added
  9. stirringThe reaction was stirred under a balloon of hydrogen for 72 h
  10. filtrationThe reaction was filtered though celite (washing with ethanol)
  11. concentrationconcentrated in vacuo
  12. custompurified by flash column (50-80% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-945f48425f244a0f908f48acbe24b21e
Source dataset
uspto-grants-2010_06
Patent number
US07728022B2

Reaction notes

Loading…