1,3-Dichloro-4,6-dinitrobenzene → 4,6-Dichlorobenzene-1,3-diamine

HRID 848034Notes

Reaction equation

HRID 848034 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([N+:11]([O-])=O)=[C:4]([Cl:14])[CH:3]=1>O1CCOCC1.[Ni]>[Cl:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([NH2:11])=[C:4]([Cl:14])[CH:3]=1

Participants

4

Reactant 1

HCID 772861,3-Dichloro-4,6-dinitrobenzene

Product 1

HCID 33728694,6-Dichlorobenzene-1,3-diamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 312751,4-DioxaneSolvent

Procedure

87.0 g (0.37 mol) of 1,3-dichloro-4,6-dinitrobenzene are dissolved in 1.5 liters of dioxane and, after adding a total of 100 g of Raney Ni, hydrogenated at 40° to 80° C. The catalyst is filtered off and washed with dioxane and the filtrate is concentrated. The product obtained in this way is recrystallised from hexane/toluene. Yield: 40.6 g; melting point 138°-141° C.

Workup

  1. customhydrogenated at 40° to 80° C
  2. filtrationThe catalyst is filtered off
  3. washwashed with dioxane
  4. concentrationthe filtrate is concentrated
  5. customThe product obtained in this way
  6. customis recrystallised from hexane/toluene

Sources & evidence

ORD record
ord-4222ef22dd51420398fd25f88472582e
Source dataset
uspto-grants-1981_10
Patent number
US04294606

Reaction notes

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