3-Chloro-2-(trifluoromethyl)phenylacetonitrile → 2-(3-Chloro-2-(trifluoromethyl)phenyl)ethanamine

HRID 1749490Notes

Reaction equation

HRID 1749490 reaction equation
[Cl:1][C:2]1[C:3]([C:11]([F:14])([F:13])[F:12])=[C:4]([CH2:8][C:9]#[N:10])[CH:5]=[CH:6][CH:7]=1>CO.[Ni]>[Cl:1][C:2]1[C:3]([C:11]([F:12])([F:13])[F:14])=[C:4]([CH2:8][CH2:9][NH2:10])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 1181621683-Chloro-2-(trifluoromethyl)phenylacetonitrile

Product 1

HCID 1181622402-(3-Chloro-2-(trifluoromethyl)phenyl)ethanamineYield 14.8%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-(3-chloro-2-(trifluoromethyl)phenyl)acetonitrile (0.10 g, 3.03 mmol) in MeOH (5 mL) was added Raney-nickel (100 mg). The mixture was degassed under vacuum for 10 min, and then hydrogenated under a fully-inflated balloon at room temperature overnight. The mixture was filtered through a pad of celite and the cake was washed with MeOH (10 mL). The filtrate was concentrated under vacuum to give the crude product (100 mg). MS (ESI) m/z 224.1 [M+H]+.

Workup

  1. customThe mixture was degassed under vacuum for 10 min
  2. filtrationThe mixture was filtered through a pad of celite
  3. washthe cake was washed with MeOH (10 mL)
  4. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-c20b56427e8742739678e9fe367a72fb
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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