Water → 6,7-Dimethoxy-4-(3,4-dimethoxyphenyl)-2-(2-ethylimidazol-1-ylmethyl)quinoline-3-carboxylic acid ethyl ester

HRID 1648264

Reaktionsgleichung

Reaktionsgleichung von HRID 1648264
[H-].[Na+].[CH2:3]([C:5]1[NH:6][CH:7]=[CH:8][N:9]=1)[CH3:4].[CH2:10]([O:12][C:13]([C:15]1[C:16]([CH2:39]Cl)=[N:17][C:18]2[C:23]([C:24]=1[C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH3:34])[CH:26]=1)=[CH:22][C:21]([O:35][CH3:36])=[C:20]([O:37][CH3:38])[CH:19]=2)=[O:14])[CH3:11].O>CN(C)C=O>[CH2:10]([O:12][C:13]([C:15]1[C:16]([CH2:39][N:6]2[CH:7]=[CH:8][N:9]=[C:5]2[CH2:3][CH3:4])=[N:17][C:18]2[C:23]([C:24]=1[C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH3:34])[CH:26]=1)=[CH:22][C:21]([O:35][CH3:36])=[C:20]([O:37][CH3:38])[CH:19]=2)=[O:14])[CH3:11]

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 661302-EthylimidazoleHCID 10813243Ethyl 2-chloromethyl-4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinoline-3-carboxylate

Produkt 1

HCID 108154226,7-Dimethoxy-4-(3,4-dimethoxyphenyl)-2-(2-ethylimidazol-1-ylmethyl)quinoline-3-carboxylic acid ethyl esterAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Oily sodium hydride (60%, 0.323 g) was added to a solution of 2-ethylimidazole (0.776 g) in N,N-dimethylformamide (30 ml), followed by stirring at room temperature for 15 minutes. Then 2-chloromethyl-6,7-dimethoxy-4-(3,4-dimethoxyphenyl)quinoline-3-carboxylic acid ethyl ester (3.0 g) was added. After stirring at 80° C. for 1 hour, the reaction mixture was poured over water, and the separating crystal was collected by filtration, which was then recrystallized from ethanol to yield 6,7-dimethoxy-4-(3,4-dimethoxyphenyl)-2-(2-ethylimidazol-1-ylmethyl)quinoline-3-carboxylic acid ethyl ester (2.5 g, 74%) as a colorless prismatic crystal having a melting point of 163° to 164° C.

Aufarbeitung

  1. stirringAfter stirring at 80° C. for 1 hour
  2. filtrationthe separating crystal was collected by filtration, which
  3. customwas then recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-323bdf50fd734d54861ffa4ea8d66fd0
Quelldatensatz
uspto-grants-1995_07
Patentnummer
US05436247

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