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

HRID 1416121Notes

Reaction equation

HRID 1416121 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.

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-a70d15fac5e5453393d977f63aa03f61
Source dataset
uspto-grants-1999_06
Patent number
US05910495

Reaction notes

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