Methanol → 2-(Indol-3-yl)-4-carboxy-6,7-dimethoxyquinoline

HRID 582431Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 582431
C1(S([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([C:19]3[CH:28]=[C:27]([C:29]([OH:31])=[O:30])[C:26]4[C:21](=[CH:22][C:23]([O:34][CH3:35])=[C:24]([O:32][CH3:33])[CH:25]=4)[N:20]=3)=[CH:11]2)(=O)=O)C=CC=CC=1.C([O-])([O-])=O.[K+].[K+].CO>O>[NH:10]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:12]([C:19]2[CH:28]=[C:27]([C:29]([OH:31])=[O:30])[C:26]3[C:21](=[CH:22][C:23]([O:34][CH3:35])=[C:24]([O:32][CH3:33])[CH:25]=3)[N:20]=2)=[CH:11]1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 187886132-(N-phenylsulfonylindol-3-yl)-4-carboxy-6,7-dimethoxyquinoline

Produkt 1

HCID 187887092-(Indol-3-yl)-4-carboxy-6,7-dimethoxyquinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A stirred solution of (0.547 g) of 2-(N-phenylsulfonylindol-3-yl)-4-carboxy-6,7-dimethoxyquinoline, K2CO3 (0.380 g), MeOH (40 ml) and H2O (10 ml) are heated to reflux. The MeOH is evaporated in vacuo, and the aqueous residue diluted with more H2O, and acidified with 0.IN HCl to pH between 6°-7 while contained in an ice-bath. An orange solid precipitates. This is collected, washed with ether then dried under vacuum (0.1 mm at 22° C.) for a few hours to obtain 2-(indol-3-yl)-4-carboxy-6,7-dimethoxyquinoline m.p. 286° C. dec).

Aufarbeitung

  1. customThe MeOH is evaporated in vacuo
  2. additionthe aqueous residue diluted with more H2O
  3. customto pH between 6°
  4. customwhile contained in an ice-bath
  5. customAn orange solid precipitates
  6. customThis is collected
  7. washwashed with ether
  8. customthen dried under vacuum (0.1 mm at 22° C.) for a few hours

Quellen und Nachweise

ORD-Eintrag
ord-45e27e896a2540d88e0893246939c8c5
Quelldatensatz
uspto-grants-1999_07
Patentnummer
USRE036256

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