4-Fluoro-2-(trifluoromethyl)benzonitrile → (4-Fluoro-2-(trifluoromethyl)phenyl)methanamine

HRID 1898319Notes

Reaction equation

HRID 1898319 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([C:10]([F:13])([F:12])[F:11])[CH:3]=1>C(O)C.[Ni]>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH2:7])=[C:4]([C:10]([F:11])([F:12])[F:13])[CH:3]=1

Participants

4

Reactant 1

HCID 6050854-Fluoro-2-(trifluoromethyl)benzonitrile

Product 1

HCID 2734878(4-Fluoro-2-(trifluoromethyl)phenyl)methanamineYield 19.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-fluoro-2-(trifluoromethyl)benzonitrile (2.0 g) in ethanol (10.0 mL) was added Raney Ni (catalytic amount). The reaction mixture was subjected for hydrogenation in Parr apparatus under 50 psi for 2-3 h. The reaction mass filtered through celite and concentrated the filtrate to afford 0.400 g of the desired product. 1HNMR (CDCl3): δ 3.98 (s, 2H), 7.24 (t, J=9.0 Hz, 1H), 7.34 (d, J=8.7 Hz, 1H), 7.54 (t, J=7.8 Hz, 1H); MS [M+H]+: 194.03.

Workup

  1. filtrationThe reaction mass filtered through celite
  2. concentrationconcentrated the filtrate

Sources & evidence

ORD record
ord-4a2ab3fcbc8f4e71858019d1874ba90b
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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