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

HRID 1670471Notes

Reaction equation

HRID 1670471 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]>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

4

Reactant 1

HCID 8236152-Methyl-2-(4-nitrophenyl)propanenitrile

Product 1

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

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

16 g (84.1 mmol) of 2-methyl-2-(4-nitro-phenyl)-propionitrile (Example 1d) and 4.16 g of Raney-Ni are shacked in 160 ml of THF-MeOH (1:1) under 1.1 bar of H2 for 12 h at rt. After completion of the reaction, the catalyst is filtered-off and the filtrate is evaporated to dryness. The residue is purified by flash chromatography on silica gel (hexane-EtOAc 3:1 to 1:2) to provide the title compound as an oil. ES-MS: 161 (M+H)+; analytical HPLC: tret=2.13 minutes (Grad 1).

Workup

  1. customAfter completion of the reaction
  2. customthe filtrate is evaporated to dryness
  3. customThe residue is purified by flash chromatography on silica gel (hexane-EtOAc 3:1 to 1:2)

Sources & evidence

ORD record
ord-5b5c6d3a9d4d41aea592c1ed3926a7e2
Source dataset
uspto-grants-2011_08
Patent number
US07994170B2

Reaction notes

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