Sodium Hydroxide → 4-Bromobenzene-1,2-diamine

HRID 964611Notes

Reaction equation

HRID 964611 reaction equation
[N+:1]([C:4]1[CH:10]=[C:9]([Br:11])[CH:8]=[CH:7][C:5]=1[NH2:6])([O-])=O.Cl[Sn]Cl.[OH-].[Na+]>C(O)C>[Br:11][C:9]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([NH2:1])[CH:10]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 701324-Bromo-2-nitroaniline

Product 1

HCID 3235934-Bromobenzene-1,2-diamineYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 2-nitro-4-bromoaniline (340 mg, 1.57 mmol) in absolute ethanol (20 mL) was added SnCl2 (1.50g, 7.91 mmol) and refluxed overnight. The reaction mixture was then basified to pH 11 with 2N NaOH and extracted with ether to give 275 mg (94%) of product. This product was used without further purification for the synthesis of JSK IV-37.

Workup

  1. temperaturerefluxed overnight
  2. extractionextracted with ether

Sources & evidence

ORD record
ord-ddb70cba94cb4f4c90595fee533680c3
Source dataset
uspto-grants-1998_06
Patent number
US05770617

Reaction notes

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