Benzenamine, 4-butyl-2-nitro- → 4-Butyl-1,2-benzenediamine

HRID 2071796Notes

Reaction equation

HRID 2071796 reaction equation
[CH2:1]([C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[C:7]([N+:12]([O-])=O)[CH:6]=1)[CH2:2][CH2:3][CH3:4].[H][H]>[Pt]=O.C(O)C>[CH2:1]([C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[C:7]([NH2:12])[CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 77229Benzenamine, 4-butyl-2-nitro-HCID 178418361HCID 178418361, compound

Product 1

HCID 193134-Butyl-1,2-benzenediamine

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

4-n-Butyl-2-nitroaniline (12.5 g, 0.065 mole), platinum oxide (0.75 g) and ethanol (125 ml) were mixed together and shaken in an atmosphere of hydrogen at atmospheric pressure and laboratory temperature. After six hours 5.2 liters of hydrogen had been absorbed. The mixture was filtered and ethanol removed from the filtrate by distillation. Benzene (40 ml) was added to the residual oil and this was then also removed by distillation. The crude 4-n-butyl-1,2-phenylenediamine thus obtained was used directly in the preparation of 1,2-bis-(3-methoxycarbonyl-2-thioureiddo)-4-n-butylbenzene.

Workup

  1. customAfter six hours 5.2 liters of hydrogen had been absorbed
  2. filtrationThe mixture was filtered
  3. customethanol removed from the filtrate by distillation
  4. additionBenzene (40 ml) was added to the residual oil
  5. customthis was then also removed by distillation

Sources & evidence

ORD record
ord-4ba910cc54b6407cbda5ea33e28d115c
Source dataset
uspto-grants-1977_09
Patent number
US04048326

Reaction notes

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