5-bromo-N-methyl-2-nitroaniline → 5-Bromo-N1-methylbenzene-1,2-diamine

HRID 2037808Notes

Reaction equation

HRID 2037808 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N+:10]([O-])=O)=[C:6]([NH:8][CH3:9])[CH:7]=1>[Ni].O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:10])=[C:6]([NH:8][CH3:9])[CH:7]=1

Participants

4

Reactant 1

HCID 106095305-bromo-N-methyl-2-nitroaniline

Product 1

HCID 121982705-Bromo-N1-methylbenzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (5-bromo-2-nitro-phenyl)-methyl-amine (2.60 g) and Raney nickel (0.25 g) in tetrahydrofuran (100 mL) was shaken under hydrogen atmosphere (50 psi) at room temperature overnight. Then, the catalyst was separated by filtration and the filtrate was concentrated under reduced pressure to give the crude title compound as a brown oil that was used without further purification.

Workup

  1. customThen, the catalyst was separated by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c80de943e791483586afaf1325951ee8
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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