4-Amino-3-cyanobenzotrifluoride → 2-(Aminomethyl)-4-(trifluoromethyl)aniline

HRID 17031Notes

Reaction equation

HRID 17031 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[C:4]#[N:5].[H][H].C(OCC)(=O)C.CCCCCC>C(O)C.[OH-].[NH4+].[Ni]>[NH2:5][CH2:4][C:3]1[CH:6]=[C:7]([C:10]([F:12])([F:13])[F:11])[CH:8]=[CH:9][C:2]=1[NH2:1]

Participants

7

Reactant 3

HCID 126273614-Amino-3-cyanobenzotrifluorideHCID 21226206Ethyl acetate hexaneHCID 178418361HCID 178418361, compound

Product 1

HCID 265967342-(Aminomethyl)-4-(trifluoromethyl)aniline

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 14923Ammonium HydroxideSolvent

Procedure

In a rocker shaker was charged 37 g (0.2 mol) of 2-amino-5-(trifluoromethyl)benzonitrile in 500 mL of ethanol and 76 mL of ammonium hydroxide. The contents were degassed/blanketed with nitrogen, 25 g of Raney nickel were added, then the shaker was pressurized with 40 psi hydrogen gas. At 15 hours TLC analysis (20/80 ethyl acetate/hexane) revealed no starting material. The contents were filtered through Celite and washed with ether and concentrated to 37 g black oil. The oil was chromatographed on a Biotage 75L cartridge with methanol/methylene chloride and ammonium hydroxide/methanol/methylene chloride to give [2-(aminomethyl)-4-(trifluoromethyl)phenyl]amine as a green oil.

Workup

  1. additionwere added
  2. filtrationThe contents were filtered through Celite
  3. washwashed with ether
  4. concentrationconcentrated to 37 g black oil
  5. customThe oil was chromatographed on a Biotage 75L cartridge with methanol/methylene chloride and ammonium hydroxide/methanol/methylene chloride

Sources & evidence

ORD record
ord-0d61e052b1264cb99d9f5f742412f69f
Source dataset
uspto-grants-2010_06
Patent number
US07737295B2

Reaction notes

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