1-Bromo-2-methyl-4-nitrobenzene → 4-Bromo-3-methylaniline

HRID 602440Notes

Reaction equation

HRID 602440 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[CH3:11]>[Ni].CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[CH3:11]

Participants

4

Reactant 1

HCID 2516721-Bromo-2-methyl-4-nitrobenzene

Product 1

HCID 233594-Bromo-3-methylanilineYield 99%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Activated Raney Nickel® (0.4 g) was added to a suspension of 1-bromo-2-methyl-4-nitrobenzene (4 g, 18.51 mmol) in 200 mL of methanol and the mixture was stirred under hydrogen atmosphere (30 psi) for 3 hours. After this time, the reaction mixture was filtered through Celite®, the solvent eliminated under reduced pressure and the residue dried under vacuum to afford the title compound (3.4 g, 99%) as a white solid.

Workup

  1. filtrationAfter this time, the reaction mixture was filtered through Celite®
  2. customthe residue dried under vacuum

Sources & evidence

ORD record
ord-2bbb4ca661804b54af2d60a490200d6e
Source dataset
uspto-grants-2011_03
Patent number
US07906530B2

Reaction notes

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