Hydroxyamine hydrochloride → HCID 86647341, compound

HRID 1880734Notes

Reaction equation

HRID 1880734 reaction equation
C(=O)(O)[O-:2].[Na+].Cl.NO.[F:9][C:10]([F:22])([F:21])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][N:16]=[C:15]([C:19]#[N:20])[CH:14]=1>C(O)C>[F:22][C:10]([F:9])([F:21])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][N:16]=[C:15]([C:19]([NH2:20])=[O:2])[CH:14]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 59570383HCID 59570383, compound

Product 1

HCID 86647341HCID 86647341, compoundYield 98.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 6 ml of ethanol were added 0.54 g of sodium bicarbonate and 0.45 g of hydroxylamine hydrochloride, and the mixture was heated to reflux for 1 hour. After allowing to cool, 0.65 g of 4-(2,2,2-trifluoroethoxy)pyridine-2-carbonitrile was added at room temperature, and the mixture was stirred for 10 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 washed with hexane three times to obtain 0.7 g of 4-(2,2,2-trifluoroethoxy)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
  10. washThe residue was washed with hexane three times

Sources & evidence

ORD record
ord-f8a6a6f27b1c456586378e14c3bad2e7
Source dataset
uspto-grants-2012_11
Patent number
US08318776B2

Reaction notes

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