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

HRID 412614Notes

Reaction equation

HRID 412614 reaction equation
[N+:1]([C:4]1[CH:10]=[C:9]([C:11]#[N:12])[CH:8]=[CH:7][C:5]=1[NH2:6])([O-])=O>C(O)C.[C].[Pd]>[NH2:1][C:4]1[CH:10]=[C:9]([CH:8]=[CH:7][C:5]=1[NH2:6])[C:11]#[N:12]

Participants

4

Reactant 1

HCID 5959014-Amino-3-nitrobenzonitrile

Product 1

HCID 7372853,4-DiaminobenzonitrileYield 26.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

2-Nitro-4-cyanoaniline (2.21 g) was hydrogenated using 7.5% palladium carbon (320 mg) in ethanol (44 ml) at atmospheric pressure over 2 hours. After completion of the reaction, the reaction mixture was filtered through celite, and the solvent was evaporated. To the obtained residue was added chloroform and the resultant solid was collected by filtration and dried under reduced pressure to give the title compound (474 mg).

Workup

  1. customover 2 hours
  2. customAfter completion of the reaction
  3. filtrationthe reaction mixture was filtered through celite
  4. customthe solvent was evaporated
  5. additionTo the obtained residue was added chloroform
  6. filtrationthe resultant solid was collected by filtration
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-3c5e7b932e2c4c7fbc0b6d40e2d2d1dc
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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