5-(Trifluoromethyl)pyridine-2-carbonitrile → [5-(Trifluoromethyl)pyridin-2-yl]methanamine

HRID 1181383Notes

Reaction equation

HRID 1181383 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][N:4]=1)#[N:2]>C(O)C.[OH-].[NH4+].[Ni]>[NH2:2][CH2:1][C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:10])[F:11])=[CH:5][N:4]=1

Participants

5

Reactant 1

HCID 15353725-(Trifluoromethyl)pyridine-2-carbonitrile

Product 1

HCID 3796375[5-(Trifluoromethyl)pyridin-2-yl]methanamineYield 30.5%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 14923Ammonium HydroxideSolvent

Procedure

To a nitrogen flushed solution of 2-cyano-5-(trifluoromethyl)pyridine (Description 1; 8.0 g, 46.5 mmol) in a mixture of ethanol (100 ml) and ammonium hydroxide (25 ml) was added a spatula end of Raney Nickel and the resulting mixture hydrogenated at 50 psi overnight. The catalyst was removed by filtration and the filtrate was evaporated to dryness. The residue was purified by column chromatography on silica eluting with a gradient rising from 2% MeOH in dichloromethane+0.5% NH4OH to 5% MeOH in dichloromethane+0.5% NH4OH to give the title compound (2.5 g, 30%) as a yellow oil.

Workup

  1. customhydrogenated at 50 psi overnight
  2. customThe catalyst was removed by filtration
  3. customthe filtrate was evaporated to dryness
  4. customThe residue was purified by column chromatography on silica eluting with a gradient

Sources & evidence

ORD record
ord-8b793d41cda548b9a29289ee00b56bb1
Source dataset
uspto-grants-2007_10
Patent number
US07285563B2

Reaction notes

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