Ammonia → 1-[4-(Trifluoromethyl)pyridin-3-yl]methanamine

HRID 1922011Notes

Reaction equation

HRID 1922011 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[C:9]#[N:10].N.CO.[H][H]>[Ni]>[F:11][C:2]([F:1])([F:12])[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[CH2:9][NH2:10]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 887MethanolHCID 27367434-(trifluoromethyl)nicotinonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 35238171-[4-(Trifluoromethyl)pyridin-3-yl]methanamineYield 108.4%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

To a mixture of 4-(trifluoromethyl)-3-pyridinecarbonitrile (9.5 g, 55 mmol, 1.0 equiv) and 5 M NH3 in methanol (600 mL, 3.0 mol, 54 equiv) was added Raney-Ni (3.0 g, 52 mmol, 0.95 equiv). The flask was fitted with a hydrogen balloon, and the mixture was stirred for 16 h. The reaction mixture was filtered, and the filtrate was concentrated. The residue was purified by HPLC to afford 10.5 g (47%) of the title compound as the bis-trifluoroacetate salt. MS (ES+): m/e 177.1 [M+H]+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-91c87df7cc334a8d9ecf21f74b1855ee
Source dataset
uspto-grants-2012_05
Patent number
US08173805B2

Reaction notes

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