Sodium Acetate → 5-Amino-2-(trifluoromethyl)pyridine

HRID 1976067Notes

Reaction equation

HRID 1976067 reaction equation
[NH2:1][C:2]1[C:3](Cl)=[N:4][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:7]=1.C([O-])(=O)C.[Na+].[H][H]>[Pd].CO>[NH2:1][C:2]1[CH:3]=[N:4][C:5]([C:8]([F:11])([F:9])[F:10])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 27376462-Chloro-6-(trifluoromethyl)pyridin-3-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 27377445-Amino-2-(trifluoromethyl)pyridineYield 92.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

3-Amino-2-chloro-6-trifluoromethylpyridine (15.0 g, 76 mmol), sodium acetate (12.53 g, 153 mmol) and 10% palladium on carbon (1.5 g) in methanol (300 ml) were hydrogenated at 50 psi hydrogen for 18 h, then the suspension was filtered. The filtrate was concentrated to give the product as a tan solid (11.38 g, 70 mmol, 92% yield).

Workup

  1. filtrationthe suspension was filtered
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-f9d3b9e44e944f889704e0cd0e48c9b4
Source dataset
uspto-grants-2001_05
Patent number
US06225320B1

Reaction notes

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