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

HRID 1087993

Reaction equation

HRID 1087993 reaction equation
N#CN.C(O)(=O)C.C(O)(=O)C.C(N)=N.[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][C:17]=1[N+:25]([O-])=O>[Ni].CO>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][C:17]=1[NH2:25]

Participants

7

Reactant 4

HCID 61-Chloro-2,4-DinitrobenzeneHCID 176Acetic AcidHCID 9864Cyanamide2×HCID 160693Formamidine acetate

Product 1

HCID 212094-Chloro-M-phenylenediamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

1.5 g of cyanamide, 1.5 g of acetic acid, 2 g of Raney nickel (60%, aqueous), and 120 ml of methanol are introduced in an autoclave equipped with gas introduction stirrer. Under a hydrogen pressure of 4 bar and a temperature of 25° C., the cyanamide is hydrogenated quantitatively to the formamidine acetate. 40.8 g of 1-chloro-2,4-dinitrobenzene are then added to the autoclave, and the hydrogenation is carried out at a pressure of 10 bar and a temperature of 60° C. The hydrogenation time is 1 hour. 1-Chloro-2,4-diaminobenzene, 97.5% 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 25° C.
  3. customa temperature of 60° C

Sources & evidence

ORD record
ord-854f343b508f4d689cd02c64dc88fc11
Source dataset
uspto-grants-1990_10
Patent number
US04960936

Linked notes

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