P-Phenylenediamine → 1,2,4-Triaminobenzene

HRID 236845Notes

Reaction equation

HRID 236845 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[CH:6][C:5]=1[N:13]=NC1C=CC([N+]([O-])=O)=CC=1)([O-])=O.C1C(N)=CC=C(N)C=1>C(O)C>[NH2:13][C:5]1[CH:6]=[CH:7][C:8]([NH2:10])=[CH:9][C:4]=1[NH2:1]

Participants

4

Reactant 2

HCID 7814P-PhenylenediamineHCID 2131545163436-97-5

Product 1

HCID 692061,2,4-TriaminobenzeneYield 86.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 500 ml autoclave equipped with a stirrer and a gas-introducing tube was charged with 9.5 g of 2,4,4'-trinitroazobenzene, 0.6 g of PtO and 100 ml of ethanol. The inside of the reactor was purged completely with hydrogen, and the reaction was performed at 80° C. for 6 hours with stirring while maintaining the pressure of hydrogen at 70 kg/cm2.G. The reaction mixture was filtered. The cake was washed with water. The wash liquid and the filtrate were combined, and distilled to afford 2.5 g of a fraction having a boiling point of 174° to 180° C./30 mmHg.ab. This fraction coincided with p-phenylenediamine as a standard product. The distillation residue was recrystallized from chloroform to afford 3.2 g of 1,2,4-triaminobenzene having a melting point of 93° to 96° C. This product corresponded in IR spectrum with a standard product.

Workup

  1. customA 500 ml autoclave equipped with a stirrer and a gas-introducing tube
  2. customThe inside of the reactor was purged completely with hydrogen
  3. temperaturewhile maintaining the pressure of hydrogen at 70 kg/cm2
  4. filtrationThe reaction mixture was filtered
  5. washThe cake was washed with water
  6. distillationdistilled
  7. customto afford 2.5 g of a fraction
  8. customThe distillation residue was recrystallized from chloroform

Sources & evidence

ORD record
ord-afaadfe949e64a3a8816417a095d114a
Source dataset
uspto-grants-1979_06
Patent number
US04158002

Reaction notes

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