Réaction #10646

ord-fcdc390576094c1d8a9ce9abd10a933f

Équation de réaction

O.O.[Cl][Sn][Cl]
Tin(II) chloride dihydrate
O=[N+]([O-])c1cccc2cncc(Cl)c12
Intermediate 89
O=[N+]([O-])c1cccc2cncc(Cl)c12
4-chloro-5-nitroisoquinoline
[Na+].[OH-]
sodium hydroxide
Nc1cccc2cncc(Cl)c12
title compound
Rendement 67.5%
Nc1cccc2cncc(Cl)c12
4-chloro-5-aminoisoquinoline
Rendement 67.5%

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Températurerefluxed
  2. 2
    Températurewith heating for 2 hours
  3. 3
    Extractionextracted twice with chloroform (20 ml for each time)
  4. 4
    SéchageThe organic layer was dried over anhydrous sodium sulfate
  5. 5
    Autrethe solvent was evaporated under reduced pressure

Mode opératoire

Tin(II) chloride dihydrate (1.70 g) was dissolved in concentrated hydrochloric acid (1 ml), added with a mixture of Intermediate 89 (315 mg) and 2 N aqueous hydrochloric acid (2 ml) with ice cooling and refluxed with heating for 2 hours. The reaction mixture was cooled to room temperature, added with 5 N aqueous sodium hydroxide (7 ml) and extracted twice with chloroform (20 ml for each time). The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain the title compound (182 mg).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US07094789B2uspto-grants-2006_08