5-(Biphenyl-3-ylaminomethylene)-2,2-dimethyl-[1,3]dioxane-4,6-dione → HCID 178418977, Verbindung

HRID 9360

Reaktionsgleichung

[C:1]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][CH:8]=[C:9]2[C:14](=[O:15])OC(C)(C)OC2=O)[CH:2]=1>C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1>[C:19]1([C:1]2[CH:2]=[C:3]3[C:4]([C:14]([OH:15])=[CH:9][CH:8]=[N:7]3)=[CH:5][CH:6]=2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

5-(Biphenyl-3-ylaminomethylene)-2,2-dimethyl-[1,3]dioxane-4,6-dione (160.2 g, 496 mmol) was dissolved in 800 mL of DOWTHERM A heat transfer fluid at 100° C. and added over 40 min by way of a cannula line to 1.3 L of preheated DOWTHERM A heat transfer fluid to 215° C. After complete addition, the reaction was held at 215° C. for 90 min and then cooled to RT. The resulting solid was collected by filtration, sequentially washed with diethyl ether (1.7 L) and acetone (500 mL), and then dried in a vacuum oven at 70° C. overnight. The resulting product (74.5 g) contained approximately 5% of the undesired isomer. This product was combined with material from a separate run (51.4 g) and slurried in 440 mL of refluxing ethanol. Filtration of the slurry while hot followed by sequential ethanol and diethyl ether rinses afforded 106.1 g of 7-phenylquinolin-4-ol as a tan solid.

Aufarbeitung

temperatureheat transfer fluid to 215° C
additionAfter complete addition
temperaturecooled to RT
filtrationThe resulting solid was collected by filtration
washsequentially washed with diethyl ether (1.7 L) and acetone (500 mL)
customdried in a vacuum oven at 70° C. overnight
filtrationFiltration of the slurry

Quellen und Nachweise

ORD-Eintrag: ord-0c1767eb462a4ef8a4aafe3f59af607c
Quelldatensatz: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07091214B2

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