Hydroxyamine hydrochloride → 6-Methyl-4-trifluoromethylpyridine-2-carboxamide

HRID 1880732Notes

Reaction equation

HRID 1880732 reaction equation
C(=O)(O)[O-:2].[Na+].Cl.NO.[CH3:9][C:10]1[N:15]=[C:14]([C:16]#[N:17])[CH:13]=[C:12]([C:18]([F:21])([F:20])[F:19])[CH:11]=1>C(O)C>[CH3:9][C:10]1[N:15]=[C:14]([C:16]([NH2:17])=[O:2])[CH:13]=[C:12]([C:18]([F:21])([F:19])[F:20])[CH:11]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 17862303HCID 17862303, compound

Product 1

HCID 866473326-Methyl-4-trifluoromethylpyridine-2-carboxamideYield 84.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 10 ml of ethanol were added 0.86 g of sodium bicarbonate and 0.71 g of hydroxylamine hydrochloride, and the mixture was heated to reflux for 1 hour. After allowing to cool, 0.8 g of 6-methyl-4-trifluoromethylpyridine-2-carbonitrile was added at room temperature, and the mixture was stirred for 12 hours, 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 0.74 g of 6-methyl-4-trifluoromethylpyridine-2-carboxamide=oxime.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 1 hour
  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-038f8c857206435da9c86ccd41a49b4f
Source dataset
uspto-grants-2012_11
Patent number
US08318776B2

Reaction notes

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