2-(4-Nitrophenyl)propanenitrile → 4-(1-Aminopropan-2-yl)aniline

HRID 222644Notes

Reaction equation

HRID 222644 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]([CH3:13])[C:11]#[N:12])=[CH:6][CH:5]=1)([O-])=O>N.CO.[Ni]>[NH2:12][CH2:11][CH:10]([C:7]1[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][CH:8]=1)[CH3:13]

Participants

4

Reactant 1

HCID 30165492-(4-Nitrophenyl)propanenitrile

Product 1

HCID 450790644-(1-Aminopropan-2-yl)anilineYield 100%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21705897Ammonia methanolSolvent

Procedure

2-(4-Nitrophenyl)propionitrile (5.0 g, 28.38 mmoL) was dissolved in a 20% NH3/methanol mixture (100 mL) and treated with Raney Nickel (24.79 g). It was then hydrogenated at 60 psi at room temperature for 4 hr. The reaction was then filtered through a nylon membrane. The filtrate was then concentrated in vacuo to give 4.26 g (100%) of the title compound. It was used without further purification. 1H NMR (300 MHz, CDCl3) δ ppm 7.00 (d, J=8.46 Hz, 2H) 6.66 (d, J=8.09 Hz, 2H) 3.58 (s, 2H) 2.71-2.85 (m, 2H) 2.56-2.70 (m, 1H) 1.20 (d, J=6.62 Hz, 3H). MS m/z (DCI) 151.0 (M+H)+.

Workup

  1. filtrationThe reaction was then filtered through a nylon membrane
  2. concentrationThe filtrate was then concentrated in vacuo

Sources & evidence

ORD record
ord-b8c4cec41bbf457ea54e189b61569283
Source dataset
uspto-grants-2012_06
Patent number
US08207350B2

Reaction notes

Loading…