2,3-Dichloronitrobenzene → 2,3-Dichloroaniline

HRID 989422Notes

Reaction equation

HRID 989422 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N+:9]([O-])=O>CO.[Ni]>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[NH2:9]

Participants

4

Reactant 1

HCID 185552,3-Dichloronitrobenzene

Product 1

HCID 118442,3-Dichloroaniline

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

2,3-Dichloronitrobenzene (800 g, 4.17 moles) was dissolved in methanol (5.6 L) and charged into an autoclave. Raney nickel (80 g, 10% w/w) was added to the solution. The reaction mixture was hydrogenated at 80 psi for 3.5 hrs at 30° C. and filtered through celite. Methanol was distilled off to give 2,3-dichloroaniline (C6H3Cl2NH2).

Workup

  1. additioncharged into an autoclave
  2. filtrationfiltered through celite
  3. distillationMethanol was distilled off

Sources & evidence

ORD record
ord-f4fdd907e895440c86337129bee8e148
Source dataset
uspto-grants-2003_10
Patent number
US06639072B1

Reaction notes

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