3-Nitrophenylacetonitrile → (3-Amino-phenyl)-acetonitrile

HRID 264038Notes

Reaction equation

HRID 264038 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11]#[N:12])[CH:7]=[CH:8][CH:9]=1)([O-])=O>CCO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH2:10][C:11]#[N:12])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 121253-Nitrophenylacetonitrile

Product 1

HCID 4847850(3-Amino-phenyl)-acetonitrileYield 80.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 3-nitrobenzeneacetonitril (8.0 g) in EtOH (100 ml) was hydrogenated at 1 atm and room temperature over 5% palladium on carbon (0.8 g) for 4 hrs. The catalyst was removed by filtration through Hyflo and the filtrate was evaporated. The residue was chromatographed, eluting with EA:Hexane (1:2) to give the title compound (5.25 g) as an orange oil. T.I.c. hexane:EA (2:1) Rf 0.45; NMR (300 MHz, CDCl3) d 3.792H,s); 3.9(2H,br); 6.7(3H,m); 7.2(H,M).

Workup

  1. customThe catalyst was removed by filtration through Hyflo
  2. customthe filtrate was evaporated
  3. customThe residue was chromatographed
  4. washeluting with EA:Hexane (1:2)

Sources & evidence

ORD record
ord-6f6ba0f050594fb5834682862a4f5dd8
Source dataset
uspto-grants-1997_07
Patent number
US05646140

Reaction notes

Loading…