4-Bromo-2-methyl-6-nitroaniline → 5-Bromo-3-methylbenzene-1,2-diamine

HRID 1422208Notes

Reaction equation

HRID 1422208 reaction equation
[Br:1][C:2]1[CH:8]=[C:7]([N+:9]([O-])=O)[C:5]([NH2:6])=[C:4]([CH3:12])[CH:3]=1>C(O)C.[Ni]>[Br:1][C:2]1[CH:8]=[C:7]([NH2:9])[C:5]([NH2:6])=[C:4]([CH3:12])[CH:3]=1

Participants

4

Reactant 1

HCID 5226794-Bromo-2-methyl-6-nitroaniline

Product 1

HCID 15163975-Bromo-3-methylbenzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A solution of 15 g (64.9 mmol) of 4-bromo-2-methyl-6-nitro-aniline in 300 ml of ethanol is hydrogenated in the presence of 1.5 g of Raney nickel for 4 hours at approximately 27° C. The reaction mixture is then filtered and concentrated by evaporation. The title compound is obtained in the form of a brown oil.

Workup

  1. filtrationThe reaction mixture is then filtered
  2. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-eafa51fd45cf4cb28512b5acba8d1364
Source dataset
uspto-grants-2000_06
Patent number
US06080743

Reaction notes

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