4-Amino-2-(trifluoromethyl)benzonitrile → HCID 56604265, compound

HRID 1640148Notes

Reaction equation

HRID 1640148 reaction equation
[NH2:1][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>N.CO.[Ni].C(Cl)Cl>[NH2:7][CH2:6][C:5]1[CH:8]=[CH:9][C:2]([NH2:1])=[CH:3][C:4]=1[C:10]([F:11])([F:12])[F:13]

Participants

6

Reactant 1

HCID 5221704-Amino-2-(trifluoromethyl)benzonitrile

Product 1

HCID 56604265HCID 56604265, compound

Reagents, catalysts & solvents 4

HCID 935NickelCatalystHCID 222AmmoniaSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-amino-2-(trifluoromethyl)benzonitrile (5.0 g, 26.7 mmol) in 7.0 M ammonia in MeOH (20.0 mL) was added Raney Nickel 2800 (50% slurry in water, 320 mg). The mixture was allowed to stir under an atmosphere of hydrogen for 18 h, then at 50 psi for 18 h. The mixture was diluted with DCM and filtered through Celite. The filtrate was evaporated and the residue was purified by column chromatography on silica to 4-(aminomethyl)-3-(trifluoro-methyl)aniline as an orange solid (3.43 g, 67%). LCMS: (FA) ES+ 187.1 ES− 185.2.

Workup

  1. waitat 50 psi for 18 h
  2. filtrationfiltered through Celite
  3. customThe filtrate was evaporated
  4. customthe residue was purified by column chromatography on silica to 4-(aminomethyl)-3-(trifluoro-methyl)aniline as an orange solid (3.43 g, 67%)

Sources & evidence

ORD record
ord-7aee6f5526584e3d8913efe23466ada5
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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