Benzonitrile, 3,5-dinitro- → 3,5-Diaminobenzonitrile

HRID 2071014Notes

Reaction equation

HRID 2071014 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([N+:12]([O-])=O)[CH:11]=1)[C:7]#[N:8])([O-])=O>CCO.[OH-].[OH-].[Pd+2]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([NH2:12])[CH:11]=1)[C:7]#[N:8]

Participants

4

Reactant 1

HCID 20062Benzonitrile, 3,5-dinitro-

Product 1

HCID 128973293,5-Diaminobenzonitrile

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

20% Pd(OH)2 (0.13 g) was added to a stirred suspension of 3,5-dinitrobenzonitrile (0.50 g, 2.59 mmol, 1 eq, Aldrich) in 10 ml EtOH. A H2 balloon was added. After stirring over the weekend the mixture was filtered through Celite. The filter cake was rinsed with EtOH (×3). The organics were removed in vacuo. The residue was stirred in CHCl3 and the resulting mixture was filtered (×3). The CHCl3 fractions were combined, and the solvent was removed in vacuo to yield crude 3,5-diaminobenzonitrile.

Workup

  1. additionA H2 balloon was added
  2. filtrationwas filtered through Celite
  3. washThe filter cake was rinsed with EtOH (×3)
  4. customThe organics were removed in vacuo
  5. stirringThe residue was stirred in CHCl3
  6. filtrationthe resulting mixture was filtered (×3)
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-c04d369ae6f747b0945e29a22a132844
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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