5-Hydroxyindole → 6-Methoxycarbonyl-7-methoxy-4-(5-indolyloxy)quinoline

HRID 387973Notizen

Reaktionsgleichung

Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:16][CH3:17])=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[OH:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[NH:24][CH:23]=[CH:22]2.C(N(C(C)C)CC)(C)C>CN1CCCC1=O>[CH3:15][O:14][C:12]([C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:16][CH3:17])[N:5]=[CH:4][CH:3]=[C:2]2[O:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[NH:24][CH:23]=[CH:22]2)=[O:13]

Komponenten

Reaktionsbedingungen

Temperatur: 130 °C

Versuchsvorschrift

After mixing methyl 4-chloro-7-methoxyquinoline-6-carboxylate (WO0050405, P. 34, 8.5 g, 33.77 mmol), 5-hydroxyindole (7 g), diisopropylethylamine (8.9 ml) and N-methylpyrrolidone (8.9 ml), the mixture was heated and stirred at 130° C. for 5 hours and then at 150° C. for 8 hours. After cooling, the solution was adsorbed onto silica gel and purified with a silica gel column (hexane-ethyl acetate system). Ethanol, diethyl ether and hexane were added to the obtained yellow oil, and crystals precipitated upon standing. These were filtered out, washed with diethyl ether and hexane and dried by aspiration to obtain light yellow crystals (3.506 g, 10.06 mmol, 29.80%).

Aufarbeitung

temperaturethe mixture was heated
waitat 150° C. for 8 hours
temperatureAfter cooling
custompurified with a silica gel column (hexane-ethyl acetate system)
additionEthanol, diethyl ether and hexane were added to the obtained yellow oil, and crystals
customprecipitated
filtrationThese were filtered out
washwashed with diethyl ether and hexane
customdried by aspiration

Quellen und Nachweise

ORD-Eintrag: ord-96b2c3dacce94d768343c16293e79acc
Quelldatensatz: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08372981B2

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