Ethanol → 1-(2-Chloro-4-fluorophenyl)-2-(5-trifluoromethyl-2-pyridinyl)ethanone oxime

HRID 354249Notes

Reaction equation

HRID 354249 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9](=O)[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][N:12]=1.[NH2:22][OH:23].C(N(CC)CC)C.C(O)C>C(OCC)C.C1CCCCC1>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9](=[N:22][OH:23])[CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][N:12]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 787HydroxylamineHCID 8471TriethylamineHCID 235133431-(2-Chloro-4-fluorophenyl)2-(5-trifluoromethyl-2-pyridinyl)ethanone

Product 1

HCID 865902141-(2-Chloro-4-fluorophenyl)-2-(5-trifluoromethyl-2-pyridinyl)ethanone oximeYield 36.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8078CyclohexaneSolvent

Procedure

A reaction vessel was charged with 1-(2-chloro-4-fluorophenyl)-2-(5-trifluoromethyl-2-pyridinyl)ethanone (6 g, 18.9 mmol), hydroxylamine (2.63 g, 37.8 mmol), triethylamine (5.3 m 37.8 mmol) and ethanol (60 ml). The reaction mixture was heated to reflux with stirring for 24 hrs. It was then cooled to room temperature, silica gel (about 25 g) was added and the mixture concentrated to dryness. Purification via column chromatography on silica eluting with diethylether-cyclohexane (3:7) and concentration of the appropriate fractions afforded an oil which solidified on standing. Trituration with cyclohexane containing a little diethylether afforded a solid which was removed by filtration and washed with cyclohexane to provide 2.27 g (28%) of the title compound.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. additionsilica gel (about 25 g) was added
  4. concentrationthe mixture concentrated to dryness
  5. customPurification via column chromatography on silica eluting with diethylether-cyclohexane (3:7) and concentration of the appropriate fractions
  6. customafforded an oil which
  7. customwas removed by filtration
  8. washwashed with cyclohexane

Sources & evidence

ORD record
ord-46231e3fa22f4f9ca5d9e6d230000ce5
Source dataset
uspto-grants-2004_06
Patent number
US06756498B2

Reaction notes

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