(4-Bromo-2-methoxy-6-nitro-phenyl)-(2-methoxy-ethyl)-amine → 5-bromo-3-methoxy-2-N-(2-methoxyethyl)benzene-1,2-diamine

HRID 1661902Notes

Reaction equation

HRID 1661902 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[C:5]([NH:11][CH2:12][CH2:13][O:14][CH3:15])=[C:4]([O:16][CH3:17])[CH:3]=1>C1COCC1.[Ni]>[Br:1][C:2]1[CH:7]=[C:6]([NH2:8])[C:5]([NH:11][CH2:12][CH2:13][O:14][CH3:15])=[C:4]([O:16][CH3:17])[CH:3]=1

Participants

4

Reactant 1

HCID 57772042(4-Bromo-2-methoxy-6-nitro-phenyl)-(2-methoxy-ethyl)-amine

Product 1

HCID 577720825-bromo-3-methoxy-2-N-(2-methoxyethyl)benzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6.19 (20 mmol) (4-bromo-2-methoxy-6-nitro-phenyl)-(2-methoxy-ethyl)-amine in 140 ml THF is hydrogenated in the presence of 1.4 g Raney-Nickel (B113W Degussa) at normal pressure for 25 h. The catalyst is filtered off and the filtrate is concentrated in vacuo. The residue is purified by flash-chromatography on silica gel (hexane:EtOAc=2:1) to afford 4.95 g of the title compound as a as a reddish oil.

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe filtrate is concentrated in vacuo
  3. customThe residue is purified by flash-chromatography on silica gel (hexane:EtOAc=2:1)

Sources & evidence

ORD record
ord-62abb3ed1ef042eb83667e40f9e8988b
Source dataset
uspto-grants-2011_10
Patent number
US08030497B2

Reaction notes

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