Stannous Chloride → 6-Aminoquinoline-8-carboxylic acid

HRID 1756500Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1756500
[C:1]([C:4]1[CH:5]=[C:6]([N+:14]([O-])=O)[CH:7]=[C:8]2[C:13]=1[N:12]=[CH:11][CH:10]=[CH:9]2)([OH:3])=[O:2].Cl[Sn]Cl>CO>[NH2:14][C:6]1[CH:7]=[C:8]2[C:13](=[C:4]([C:1]([OH:3])=[O:2])[CH:5]=1)[N:12]=[CH:11][CH:10]=[CH:9]2

Komponenten

4

Edukt 2

HCID 24479Stannous ChlorideHCID 1501526-Nitro-8-quinolinecarboxylic acid

Produkt 1

HCID 193905666-Aminoquinoline-8-carboxylic acidAusbeute 35,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a suspension of 8-carboxy-6-nitroquinoline (4 g; 18 mM) in methanol (70 ml) was added SnCl2 (20.4 g; 90 mM). The mixture was heated to, and maintained at 40° C. until dissolution of the insoluble. After evaporation of the :solvent, the residue was taken-up in a 2M aqueous solution of NaOH and purified by subjecting to chromatography on Dowex 1X2 Resin. After basification (pH3) with concentrated NH4OH the resulting solid was further purified by subjecting to chromatography on HP20SS resin, eluting with MeOH/H2O--AcOH 1% (30.70) to give 6-amino-8-carboxyquinoline (1.2 g, 35.5%)

Aufarbeitung

  1. temperatureThe mixture was heated to, and
  2. customAfter evaporation of the :solvent
  3. custompurified
  4. customAfter basification (pH3) with concentrated NH4OH the resulting solid was further purified
  5. washeluting with MeOH/H2O--AcOH 1% (30.70)

Quellen und Nachweise

ORD-Eintrag
ord-82ce28bcf4454b319a82060f12018710
Quelldatensatz
uspto-grants-1995_08
Patentnummer
US05441949

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