2-Methyl-2-(4-nitrophenyl)propanenitrile → 2-(4-Aminophenyl)-2-methylpropanenitrile

HRID 476149Notes

Reaction equation

HRID 476149 reaction equation
[CH3:1][C:2]([C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][CH:7]=1)([CH3:5])[C:3]#[N:4].[H][H]>C1COCC1.CO.[Ni]>[NH2:12][C:9]1[CH:8]=[CH:7][C:6]([C:2]([CH3:5])([CH3:1])[C:3]#[N:4])=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 8236152-Methyl-2-(4-nitrophenyl)propanenitrile2×HCID 178418361HCID 178418361, compound

Product 1

HCID 100578012-(4-Aminophenyl)-2-methylpropanenitrile

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

2-Methyl-2-(4-nitrophenyl)propanenitrile (Compound of step 1, 16 g, 84.1 mmol) and Raney-Ni (4.16 g) were shaken in THF-MeOH [(1:1), 160 mL] under 40 psi of hydrogen for 10 hours at RT, After completion of reaction, the catalyst was filtered-off and the solvent was evaporated to dryness. The crude product was purified by column chromatography (silica gel, ethyl acetate in hexane) to obtain the title compound as oil.

Workup

  1. customAfter completion of reaction
  2. customthe solvent was evaporated to dryness
  3. customThe crude product was purified by column chromatography (silica gel, ethyl acetate in hexane)

Sources & evidence

ORD record
ord-e16033792a53478db58e3d4ca92060bd
Source dataset
uspto-grants-2014_01
Patent number
US08637670B2

Reaction notes

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