Stannous Chloride → 4-Bromobenzene-1,2-diamine

HRID 325001Notes

Reaction equation

HRID 325001 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-])=O)[CH:3]=1.Cl[Sn]Cl>C(O)C>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([NH2:9])[CH:3]=1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 701324-Bromo-2-nitroaniline

Product 1

HCID 3235934-Bromobenzene-1,2-diamineYield 94.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Bromo-2-nitroaniline 600 mg (2.76 mmol) was dissolved in 25 ml absolute ethanol and 2.72 g (14 mmol) SnCl2 was added. The mixture was refluxed overnight. Ethanol was removed in vacuo and the mixture basified with 2N NaOH to pH 11. Ether extraction, drying the ether-layer over anhydrous Na2SO4 and concentration in vacuo afforded 486 mg (2.6 mmol, 94% yield) of the crude 4-bromo-o-phenylenediamine which was used for the next step without characterization.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. customEthanol was removed in vacuo
  3. extractionEther extraction
  4. dry with materialdrying the ether-layer
  5. concentrationover anhydrous Na2SO4 and concentration in vacuo

Sources & evidence

ORD record
ord-29e3486bb5fd4d32be65c3a2bb5c819f
Source dataset
uspto-grants-2001_04
Patent number
US06221892B1

Reaction notes

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