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

HRID 1843863Notes

Reaction equation

HRID 1843863 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.[Ni].CO.C(Cl)(Cl)Cl>[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

6

Reactant 1

HCID 753594-(Trifluoromethyl)phenylacetonitrile

Product 1

HCID 19881062-[4-(Trifluoromethyl)phenyl]ethan-1-amineYield 97.89%

Reagents, catalysts & solvents 4

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 887MethanolSolvent2×HCID 6212ChloroformSolvent

Procedure

(4-Trifluoromethyl-phenyl)-acetonitrile (2 g, 10.81 mmol) in methanolic ammonia (50 mL) was added to Raney nickel (400 mg) in methanol taken in a parr hydrogenator. The flask was stirred at 50 PSI overnight. The reaction was monitored by TLC (10% methanol in CHCl3). The reaction mixture was filtered through celite bed and the filtrate was dried under reduced pressure to afford 2 g of the product (97.89% yield).

Workup

  1. filtrationThe reaction mixture was filtered through celite bed
  2. customthe filtrate was dried under reduced pressure

Sources & evidence

ORD record
ord-6c923214ae634092afebb4fceec2c304
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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