Triethylamine → 2,2,2-Trifluoro-1-(3-nitrophenyl)ethanone oxime

HRID 2307422Notes

Reaction equation

HRID 2307422 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=1)=O.[NH2:16][OH:17].Cl.CCN(CC)CC>CCO>[F:1][C:2]([F:15])([F:14])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-:13])=[O:12])[CH:6]=1)=[N:16][OH:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 695662,2,2-Trifluoro-1-(3-nitrophenyl)ethan-1-oneHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 739856852,2,2-Trifluoro-1-(3-nitrophenyl)ethanone oximeYield 79.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2,2,2-trifluoro-1-(3-nitro-phenyl)ethanone (4 g), NH2OH.HCl (5.037 g), and Et3N (20.44 g) in EtOH (80 mL) was refluxed for 4 days. After concentration, the residue was extracted with CH2Cl2. The organic layer was washed with water and dried over MgSO4. The crude product was purified by silica gel flash chromatography (30% ethyl acetate in hexanes) to give the title compound (3.4 g) as a solid.

Workup

  1. temperaturewas refluxed for 4 days
  2. concentrationAfter concentration
  3. extractionthe residue was extracted with CH2Cl2
  4. washThe organic layer was washed with water
  5. dry with materialdried over MgSO4
  6. customThe crude product was purified by silica gel flash chromatography (30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-2278fa11a07f44b9995cb43110b157c1
Source dataset
uspto-grants-2004_12
Patent number
US06831080B2

Reaction notes

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