Hydroxyamine hydrochloride → 6-Methyl-4-(2,2,2-trifluoroethoxy)pyridine-2-carboxamide

HRID 1880740Notes

Reaction equation

HRID 1880740 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]([O:18][CH2:19][C:20]([F:23])([F:22])[F:21])[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]([O:18][CH2:19][C:20]([F:23])([F:21])[F:22])[CH:11]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 595703876-Methyl-4-(2,2,2-trifluoroethoxy)pyridine-2-carbonitrile

Product 1

HCID 866473336-Methyl-4-(2,2,2-trifluoroethoxy)pyridine-2-carboxamideYield 101.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 6 ml of ethanol were added 0.54 g of sodium bicarbonate and 0.44 g of hydroxylamine hydrochloride, and the mixture was heated to reflux for 1 hour. After allowing to cool, 0.69 g of 6-methyl-4-(2,2,2-trifluoroethoxy)pyridine-2-carbonitrile was added at room temperature, and the mixture was stirred for 2 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 0.76 g of 6-methyl-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-6b0dbe7d5ceb43fe8b1fff3ebbda9f3d
Source dataset
uspto-grants-2012_11
Patent number
US08318776B2

Reaction notes

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