1-Chloro-2,4-Dinitrobenzene → 4-Chloro-M-phenylenediamine

HRID 1087988Notes

Reaction equation

HRID 1087988 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[N+:11]([O-])=O.C(O)(=O)C.C(N)=N.[H][H]>[Ni].CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[NH2:11]

Participants

6

Reactant 3

HCID 61-Chloro-2,4-DinitrobenzeneHCID 160693Formamidine acetateHCID 178418361HCID 178418361, compound

Product 1

HCID 212094-Chloro-M-phenylenediamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

40.8 g of 1-chloro-2,4-dinitrobenzene, 2 g of Raney nickel (60%, aqueous), 1.5 g of formamidine acetate and 120 ml of methanol are introduced in an autoclave equipped with gas introduction stirrer. The air in the autoclave is then displaced by nitrogen and then by hydrogen. The hydrogenation is carried out at a pressure of 10 bar and a temperature of 60° C. The hydrogenation time is 11/4 hours. 1-Chloro-2,4-diaminobenzene, 99% pure (analysed as 1-Chloro-2,4-acetamidobenzene by liquid chromatography), is obtained in quantitative yield.

Workup

  1. customequipped with gas introduction stirrer
  2. customa temperature of 60° C
  3. custom4 hours

Sources & evidence

ORD record
ord-559f18dcda8a431f96929c3468782f77
Source dataset
uspto-grants-1990_10
Patent number
US04960936

Reaction notes

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