1-Bromo-4-methoxy-2,3-dinitrobenzene → 3-Bromo-6-methoxybenzene-1,2-diamine

HRID 1661887Notes

Reaction equation

HRID 1661887 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([N+:10]([O-])=O)[C:3]=1[N+:13]([O-])=O>C1COCC1.[Ni]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[C:4]([NH2:10])[C:3]=1[NH2:13]

Participants

4

Reactant 1

HCID 577720761-Bromo-4-methoxy-2,3-dinitrobenzene

Product 1

HCID 577720123-Bromo-6-methoxybenzene-1,2-diamineYield 99.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.12 g (4.04 mmol) 1-bromo-4-methoxy-2,3-dinitro-benzene in 25 ml THF is hydrogenated in the presence of 100 mg Raney-Nickel (B113W Degussa) at normal pressure for 3 h. The catalyst is filtered off and the filtrate is concentrated in vacuo to afford 871 mg of the title compound as a grey crystalline solid.

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-bac0b83d47a84cde9905edf366c9ee3b
Source dataset
uspto-grants-2011_10
Patent number
US08030497B2

Reaction notes

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