Hydrogen Peroxide → 3-Amino-5-(trifluoromethyl)picolinamide

HRID 1775271Notes

Reaction equation

HRID 1775271 reaction equation
[OH:1]O.[NH2:3][C:4]1[C:5]([C:14]#[N:15])=[N:6][CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1.[OH-].[Na+].CO>O>[NH2:3][C:4]1[C:5]([C:14]([NH2:15])=[O:1])=[N:6][CH:7]=[C:8]([C:10]([F:13])([F:11])[F:12])[CH:9]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 887MethanolHCID 14798Sodium HydroxideHCID 135322513-Amino-5-(trifluoromethyl)pyridine-2-carbonitrile

Product 1

HCID 867281563-Amino-5-(trifluoromethyl)picolinamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2 ml of a 30% aqueous hydrogen peroxide solution was added to a mixture of 100 mg of 3-amino-2-cyano-5-trifluoromethylpyridine, 2 ml of a 10% aqueous sodium hydroxide solution and 6 ml of methanol, under ice cooling, and the mixture was stirred at room temperature for 1 hour. Water was added to the reaction mixture, and the mixture was extracted with t-butyl methyl ether. The organic layer was washed with a 10% aqueous sodium thiosulfate solution and dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure to obtain 100 mg of 3-amino-5-trifluoromethylpyridine-2-carboxylic acid amide.

Workup

  1. extractionthe mixture was extracted with t-butyl methyl ether
  2. washThe organic layer was washed with a 10% aqueous sodium thiosulfate solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-09af4913e6104d2d94f754cf10c38533
Source dataset
uspto-grants-2016_02
Patent number
US09260436B2

Reaction notes

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