4,5-Dibromo-2-nitroaniline → 4,5-Dibromobenzene-1,2-diamine

HRID 444440Notes

Reaction equation

HRID 444440 reaction equation
[Br:1][C:2]1[C:8]([Br:9])=[CH:7][C:5]([NH2:6])=[C:4]([N+:10]([O-])=O)[CH:3]=1.[H][H]>[Ni].C(O)C>[Br:1][C:2]1[C:8]([Br:9])=[CH:7][C:5]([NH2:6])=[C:4]([NH2:10])[CH:3]=1

Participants

5

Procedure

Five grams of 4,5-dibromo-2-nitroaniline were suspended in 200 ml. of anhydrous ethanol to which was added about 10 g. of Raney Nickel. The hydrogenation mixture was placed in a low pressure hydrogenation apparatus at a hydrogen pressure of 55 psi. A rapid uptake of hydrogen occurred which ceased after about 25 minutes, at which time the deep yellow color originally present was discharged indicating complete reduction of the nitro group to an amine group. The hydrogenation was continued for another half hour and the hydrogenation mixture was then worked up by filtering off the catalyst, washing the filtered catalyst, and stripping the volatile constituents from the filtrate. A yield of 4.1 g. of 4,5-dibromo-o-phenylenediamine was obtained.

Workup

  1. waitThe hydrogenation was continued for another half hour
  2. filtrationby filtering off the catalyst
  3. washwashing the filtered catalyst

Sources & evidence

ORD record
ord-d91b83f891b84430803d82b79d8f3a70
Source dataset
uspto-grants-1981_04
Patent number
US04264600

Reaction notes

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