Ethanol → 5-(Trifluoromethyl)pyridin-2-ylamidoxime

HRID 1648419Notes

Reaction equation

HRID 1648419 reaction equation
C(O)C.[C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]([F:15])([F:14])[F:13])=[CH:8][N:7]=1)#[N:5].Cl.[NH2:17][OH:18].[OH-].[Na+]>ClCCCl.O>[F:14][C:12]([F:15])([F:13])[C:9]1[CH:10]=[CH:11][C:6]([C:4](=[N:17][OH:18])[NH2:5])=[N:7][CH:8]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 14798Sodium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 15353725-(Trifluoromethyl)pyridine-2-carbonitrile

Product 1

HCID 27793275-(Trifluoromethyl)pyridin-2-ylamidoximeYield 95.3%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent2×

Procedure

180 ml of ethanol were added to a solution of 22 g of 2-cyano-5-trifluoromethylpyridine in 180 ml of 1,2-dichloroethane under stirring at room temperature, followed by drop-wise addition thereto of a solution of 9.8 g of hydroxylamine hydrochloride in 17 ml of water. An aqueous solution of 5.6 g of sodium hydroxide in 17 ml of water was drop-wise added to the resulting mixture. After completion of the drop-wise addition, the reaction mixture was heated at 80° C. for 2 hours. The reaction mixture was cooled, and stripped of insolubles by filtration. The filtrate was subjected to distillation under reduced pressure to remove therefrom the solvent. The resulting residue was washed with hexane. The precipitated solid was filtered off to obtain 25 g of 5-trifluoromethyl-2-pyridinecarboxamide oxime having a melting point of 130° to 133° C.

Workup

  1. additionfollowed by drop-wise addition
  2. additionAfter completion of the drop-wise addition
  3. temperaturethe reaction mixture was heated at 80° C. for 2 hours
  4. temperatureThe reaction mixture was cooled
  5. filtrationstripped of insolubles by filtration
  6. distillationThe filtrate was subjected to distillation under reduced pressure
  7. customto remove
  8. washThe resulting residue was washed with hexane
  9. filtrationThe precipitated solid was filtered off

Sources & evidence

ORD record
ord-54a974a1ebab475bbd9862b7a6f3d909
Source dataset
uspto-grants-1995_07
Patent number
US05436267

Reaction notes

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