2,5-Dichloronitrobenzene → 2,5-Dichloroaniline

HRID 1087990Notes

Reaction equation

HRID 1087990 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[N+:9]([O-])=O.C(O)(=O)C.C(N)=N.[H][H]>[Ni].CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[NH2:9]

Participants

6

Reactant 3

HCID 69772,5-DichloronitrobenzeneHCID 160693Formamidine acetateHCID 178418361HCID 178418361, compound

Product 1

HCID 72622,5-Dichloroaniline

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

48.0 g of 1,4-dichloro-2-nitrobenzene, 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 12 bar and a temperature of 80° C. The hydrogenation time is 1 hour. 1,4-Dichloro-2-aminobenzene, 99.6% pure (analysed by gas chromatography), is obtained in quantitative yield.

Workup

  1. customequipped with gas introduction stirrer
  2. customa temperature of 80° C

Sources & evidence

ORD record
ord-f88cfd2fe4ba4ca5a37b639364d03d64
Source dataset
uspto-grants-1990_10
Patent number
US04960936

Reaction notes

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