Hydroxyamine hydrochloride → 4-(2,2,2-Trifluoro-1-methyl-ethyl)pyridine-2-carboxamide

HRID 1880773

Reaction equation

HRID 1880773 reaction equation
C(=O)(O)[O-:2].[Na+].Cl.NO.[F:9][C:10]([F:22])([F:21])[CH:11]([C:13]1[CH:18]=[CH:17][N:16]=[C:15]([C:19]#[N:20])[CH:14]=1)[CH3:12]>C(O)C>[F:22][C:10]([F:9])([F:21])[CH:11]([C:13]1[CH:18]=[CH:17][N:16]=[C:15]([C:19]([NH2:20])=[O:2])[CH:14]=1)[CH3:12]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 595703594-(2,2,2-Trifluoro-1-methyl-ethyl)pyridine-2-carbonitrile

Product 1

HCID 866473394-(2,2,2-Trifluoro-1-methyl-ethyl)pyridine-2-carboxamideYield 102.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 7 ml of ethanol were added 0.44 g of sodium bicarbonate and 0.37 g of hydroxylamine hydrochloride, and the mixture was heated to reflux for 1 hour. After allowing to cool, 0.7 g of 4-(2,2,2-trifluoro-1-methyl-ethyl)pyridine-2-carbonitrile was added at 0° C., and the mixture was stirred for 4 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 0.78 g of 4-(2,2,2-trifluoro-1-methyl-ethyl)pyridine-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-17346a5123b34d9aa66625967188cc8a
Source dataset
uspto-grants-2012_11
Patent number
US08318776B2

Linked notes

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