Sodium Hydroxide → 4-Chloro-1,2-diaminobenzene

HRID 964612Notes

Reaction equation

HRID 964612 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:5]=1[NH2:6])([O-])=O.Cl[Sn]Cl.[OH-].[Na+]>C(O)C>[Cl:11][C:8]1[CH:9]=[CH:10][C:4]([NH2:1])=[C:5]([NH2:6])[CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 742185-Chloro-2-nitroaniline

Product 1

HCID 72634-Chloro-1,2-diaminobenzeneYield 99.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 2-nitro-5-chloroaniline (304 mg, 1.76 mmol) in absolute ethanol (20 mL) was added SnCl2 (1.68g, 8.86 mmol) and refluxed overnight. The reaction mixture was then basified to pH 11 with 2N NaOH and extracted with ether to give 250 mg (quantitative yield) of product. This product was used without further purification for the synthesis of JSK IV-68.

Workup

  1. temperaturerefluxed overnight
  2. extractionextracted with ether

Sources & evidence

ORD record
ord-be5ad23ba12d44de8c852b3631832a7b
Source dataset
uspto-grants-1998_06
Patent number
US05770617

Reaction notes

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