Hydroxyamine hydrochloride → 4-(Trifluoromethyl)picolinamide

HRID 1880717Notes

Reaction equation

HRID 1880717 reaction equation
C(=O)(O)[O-:2].[Na+].Cl.NO.[C:9]([C:11]1[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[CH:13][N:12]=1)#[N:10]>C(O)C>[F:19][C:17]([F:20])([F:18])[C:15]1[CH:14]=[CH:13][N:12]=[C:11]([C:9]([NH2:10])=[O:2])[CH:16]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 203104534-(Trifluoromethyl)pyridine-2-carbonitrile

Product 1

HCID 538130744-(Trifluoromethyl)picolinamideYield 75.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 72 ml of ethanol were added 6.18 g of sodium bicarbonate and 5.11 g of hydroxylamine hydrochloride, and the mixture was heated to reflux for 45 minutes. After allowing to cool, 6 g of 2-cyano-4-trifluoromethylpyridine was added at 0° C., and the mixture was stirred, and concentrated. To the residue was added water, the resultant solution was extracted with ethyl acetate three times, and the organic layers were combined, washed with an aqueous saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 5 g of 4-trifluoromethylpyridine-2-carboxamide=oxime.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 45 minutes
  3. temperatureto cool
  4. concentrationconcentrated
  5. additionTo the residue was added water
  6. extractionthe resultant solution was extracted with ethyl acetate three times
  7. washwashed with an aqueous saturated sodium chloride solution
  8. dry with materialdried with anhydrous magnesium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-72a8fdce4e554ebabeb163a4bdeaa872
Source dataset
uspto-grants-2012_11
Patent number
US08318776B2

Reaction notes

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