Hydrazine → 6,6′-Dimethyl[1,1′-biphenyl]-2,2′-diamine

HRID 1534194Notes

Reaction equation

HRID 1534194 reaction equation
[CH3:1][C:2]1[C:7]([C:8]2[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][C:9]=2[N+:15]([O-])=O)=[C:6]([N+:18]([O-])=O)[CH:5]=[CH:4][CH:3]=1.O.NN.NN>C(O)C.[Ni]>[CH3:14][C:13]1[C:8]([C:7]2[C:2]([CH3:1])=[CH:3][CH:4]=[CH:5][C:6]=2[NH2:18])=[C:9]([NH2:15])[CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 9321HydrazineHCID 24654Hydrazine hydrate (1:1)HCID 2929672,2'-Dinitro-6,6'-dimethylbiphenyl

Product 1

HCID 8822416,6′-Dimethyl[1,1′-biphenyl]-2,2′-diamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent2×

Procedure

The atmosphere of a 500 ml eggplant flask equipped with a three-way cock at the top and an Allihn condenser was dried under reduced pressure and displaced with nitrogen. In the flask was charged 13.6 g (50 mmole) of 6,6'-dimethyl-2,2'-dinitro-1,1'-biphenyl (7) as obtained in Preparation Example 4 and dissolved in 120 ml of warm 99% ethanol having been previously displaced with nitrogen, followed by stirring. To the mixture was added 35 ml (0.7 mole) of hydrazine hydrate having been displaced with nitrogen. A suspension of 3 ml of a Raney nickel W2 type catalyst in ethanol was slowly added thereto by means of a syringe while maintaining the activity. Thereafter, the mixture was heated at reflux in an oil bath until the whole of the hydrazine was consumed.

Workup

  1. customThe atmosphere of a 500 ml eggplant flask equipped with a three-way cock at the top
  2. customan Allihn condenser was dried under reduced pressure
  3. customas obtained in Preparation Example 4
  4. additionwas slowly added
  5. temperatureby means of a syringe while maintaining the activity
  6. temperatureThereafter, the mixture was heated
  7. customwas consumed

Sources & evidence

ORD record
ord-3bc8f723671a4999bd840bb144d800ed
Source dataset
uspto-grants-1992_02
Patent number
US05087728

Reaction notes

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