Diethyl Ether → 4-hydroxy-N,N-bis(4-methoxybenzyl)-2-oxo-1,2-dihydroquinoline-3-carboxamide

HRID 44408

Reaktionsgleichung

[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4](=[O:12])[C:3]=1[C:13]([O:15]CC)=O.[CH3:18][O:19][C:20]1[CH:36]=[CH:35][C:23]([CH2:24][NH:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)=[CH:22][CH:21]=1.C(OCC)C>C1(C)C=CC=CC=1>[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4](=[O:12])[C:3]=1[C:13]([N:25]([CH2:24][C:23]1[CH:22]=[CH:21][C:20]([O:19][CH3:18])=[CH:36][CH:35]=1)[CH2:26][C:27]1[CH:28]=[CH:29][C:30]([O:33][CH3:34])=[CH:31][CH:32]=1)=[O:15]

Komponenten

Reaktionsbedingungen

Temperatur: 115 °C

Versuchsvorschrift

Ethyl 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylate (Example 67) (3.58 g, 15.4 mmol) and bis(4-methoxybenzyl)amine (4.54 g, 17.6 mmol) were suspended in toluene (36 mL) and heated at 115° C. for 5 hours, then cooled to room temperature. Diethyl ether was added (50 mL), and the resultant precipitate was collected by filtration to give crude 4-hydroxy-N,N-bis(4-methoxybenzyl)-2-oxo-1,2-dihydroquinoline-3-carboxamide (6.45 g, 95%) which was used without further purification.

Aufarbeitung

temperaturecooled to room temperature
filtrationthe resultant precipitate was collected by filtration

Quellen und Nachweise

ORD-Eintrag: ord-5e8f1d25f7f34e829455eecd5ba20f6c
Quelldatensatz: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08541421B2

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