4-(Trifluoromethyl)phenylacetonitrile → 2-[4-(Trifluoromethyl)phenyl]ethan-1-amine

HRID 969557Notes

Reaction equation

HRID 969557 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]#[N:11])=[CH:5][CH:4]=1>N.CO.[Ni]>[F:1][C:2]([F:12])([F:13])[C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][NH2:11])=[CH:7][CH:8]=1

Participants

5

Reactant 1

HCID 753594-(Trifluoromethyl)phenylacetonitrile

Product 1

HCID 19881062-[4-(Trifluoromethyl)phenyl]ethan-1-amine

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 887MethanolSolvent

Procedure

[4-(Trifluoromethyl)phenyl]acetonitrile (10.0 g, 54 mmol) was dissolved in a 2.00 M solution of ammonia in methanol (100 mL) in a Parr flask. To it was added Raney Nickel (approx. 1 g). The mixture was shaken under hydrogen (50 psi) for 20 h and filtered through celite which was then washed with methylene chloride several times. The filtrate was concentrated to afford the title compound as a solid. MS calculated for C9H10F3N: (M+H)+190; found 173.1 (M+H−NH3)+.

Workup

  1. filtrationfiltered through celite which
  2. washwas then washed with methylene chloride several times
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-62e75511a4de4eed82ba72c30e53673b
Source dataset
uspto-grants-2007_12
Patent number
US07307086B2

Reaction notes

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