2-Methyl-2-(3-nitrophenyl)propanenitrile → 2-(3-Aminophenyl)-2-methylpropanenitrile

HRID 450042Notes

Reaction equation

HRID 450042 reaction equation
[CH3:1][C:2]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-])=O)[CH:7]=1)([CH3:5])[C:3]#[N:4]>CO.[Pd]>[NH2:12][C:8]1[CH:7]=[C:6]([C:2]([CH3:5])([CH3:1])[C:3]#[N:4])[CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 1

HCID 155413242-Methyl-2-(3-nitrophenyl)propanenitrile

Product 1

HCID 569657872-(3-Aminophenyl)-2-methylpropanenitrileYield 83.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-Methyl-2-(3-nitrophenyl)-propionitrile (0.5 g) was hydrogenated over 10% Pd—C in methanol (10 ml) at atmospheric pressure until no further gas uptake was observed. The reaction mixture was then filtered over celite and concentrated to oil. Column chromatography over silica gel by eluting with ethyl acetate/pet ether (1:9) gave 2-(3-amino-phenyl)-2-methyl-propionitrile (0.35 g, 83%) as an oil.

Workup

  1. filtrationThe reaction mixture was then filtered over celite and
  2. concentrationconcentrated to oil
  3. washColumn chromatography over silica gel by eluting with ethyl acetate/pet ether (1:9)

Sources & evidence

ORD record
ord-50019a57dca74cb8b5b61346fdd62c11
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

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