4-Amino-3-nitrobenzonitrile → 3,4-Diaminobenzonitrile

HRID 2244628Notes

Reaction equation

HRID 2244628 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:10]([O-])=O>CCO.C1COCC1.[Pd]>[NH2:10][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=1[NH2:1])[C:6]#[N:7]

Participants

4

Reactant 1

HCID 5959014-Amino-3-nitrobenzonitrile

Product 1

HCID 7372853,4-DiaminobenzonitrileYield 96.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a mixed solution of 4-amino-3-nitrobenzonitrile (8 g) in EtOH/THF (40 ml/40 ml) was added Pd—C (50% wet) (0.8 g), followed by stirring under an H2 atmosphere for 12 hours. The reaction solution was filtered through celite, and concentrated. The residue was powdered/washed with a mixed solvent of IPE and IPA, and collected by filtration to obtain 3,4-diaminobenzonitrile (6.3 g) as orange powders.

Workup

  1. filtrationThe reaction solution was filtered through celite
  2. concentrationconcentrated
  3. washThe residue was powdered/washed with a mixed solvent of IPE and IPA
  4. filtrationcollected by filtration

Sources & evidence

ORD record
ord-4a182f47ab3a47c0b5550617e5926da2
Source dataset
uspto-grants-2010_03
Patent number
US07678820B2

Reaction notes

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