Sodium Hydroxide → 1-(2,6-Difluoro-3-pyridyl)ethanamine

HRID 1436100Notes

Reaction equation

HRID 1436100 reaction equation
[F:1][C:2]1[C:7]([C:8](=[N:10]O)[CH3:9])=[CH:6][CH:5]=[C:4]([F:12])[N:3]=1.[OH-].[Na+]>FC(F)(F)C(O)=O.[Zn]>[F:1][C:2]1[C:7]([CH:8]([NH2:10])[CH3:9])=[CH:6][CH:5]=[C:4]([F:12])[N:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 866126081-(2,6-Difluoropyridin-3-yl)ethanone oxime

Product 1

HCID 690073831-(2,6-Difluoro-3-pyridyl)ethanamineYield 71.8%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

Zinc (9.29 g) was added in three portions to a solution of 1-(2,6-difluoropyridin-3-yl)ethanone oxime (2.44 g) in trifluoroacetic acid (100 mL), and the reaction solution was stirred at room temperature for two hours. The reaction solution was made basic (pH 14) with 5 N sodium hydroxide and filtered through celite, and the celite was washed with chloroform. The organic layer was separated and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to obtain 1.61 g of the title compound.

Workup

  1. filtrationfiltered through celite
  2. washthe celite was washed with chloroform
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-5a378ac3374848de99f0166cc7b6535f
Source dataset
uspto-grants-2009_11
Patent number
US07618960B2

Reaction notes

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