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

HRID 1087992

Reaction equation

HRID 1087992 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(NC=NCCCC)CCC.[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 86744256HCID 86744256, compoundHCID 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), 2.3 g of N,N'-dibutylformamidine 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, 97% 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-45196dd3922c46828428291de1cdc84c
Source dataset
uspto-grants-1990_10
Patent number
US04960936

Linked notes

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