3-Tert-butylbenzonitrile → (3-(tert-Butyl)phenyl)methanamine

HRID 2070987Notes

Reaction equation

HRID 2070987 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[C:8]#[N:9])([CH3:4])([CH3:3])[CH3:2]>CO.[OH-].[NH4+].[Ni]>[C:1]([C:5]1[CH:6]=[C:7]([CH2:8][NH2:9])[CH:10]=[CH:11][CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 1

HCID 1407313-Tert-butylbenzonitrile

Product 1

HCID 8167069(3-(tert-Butyl)phenyl)methanamine

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 887MethanolSolventHCID 14923Ammonium HydroxideSolvent

Procedure

To 3-tert-butylbenzonitrile (400 mg) in MeOH (5 mL), aqueous ammonium hydroxide (1 mL) and Raney Nickel (catalytic) were added and the reaction mixture was hydrogenated at 50 psi for 2 h. Then the reaction mixture was filtered and solvent evaporated. (3-tert-butylphenyl)methanamine was used without any purification.

Workup

  1. filtrationThen the reaction mixture was filtered
  2. customsolvent evaporated
  3. custom(3-tert-butylphenyl)methanamine was used without any purification

Sources & evidence

ORD record
ord-bbc72d039ee94c15a853aef909dfd47b
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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