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1,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene) → Ethyl 8-fluoro-6,7-dimethoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 525888
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 525888
C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1.[F:26][C:27]1[C:32]([O:33][CH3:34])=[C:31]([O:35][CH3:36])[CH:30]=[CH:29][C:28]=1[NH:37][CH:38]=[C:39]([C:45]([O:47][CH2:48][CH3:49])=[O:46])[C:40]([O:42][CH2:43][CH3:44])=[O:41]>CCCCCC>[F:26][C:27]1[C:32]([O:33][CH3:34])=[C:31]([O:35][CH3:36])[CH:30]=[CH:29][C:28]=1[NH:37][CH:38]=[C:39]([C:45]([O:47][CH2:48][CH3:49])=[O:46])[C:40]([O:42][CH2:43][CH3:44])=[O:41].[F:26][C:27]1[C:32]([O:33][CH3:34])=[C:31]([O:35][CH3:36])[CH:30]=[C:29]2[C:28]=1[NH:37][CH:38]=[C:39]([C:40]([O:42][CH2:43][CH3:44])=[O:41])[C:45]2=[O:47]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)HCID 86732752Diethyl 2-(((2-fluoro-3,4-dimethoxyphenyl)amino)methylene)malonate

Produkt 2

HCID 86732752Diethyl 2-(((2-fluoro-3,4-dimethoxyphenyl)amino)methylene)malonateHCID 86732753Ethyl 8-fluoro-6,7-dimethoxy-4-oxo-1,4-dihydroquinoline-3-carboxylateAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058
Hexane
Lösungsmittel

Versuchsvorschrift

To Dowtherm (25 mL) heated at 250° C. was added diethyl 2-(((2-fluoro-3,4-dimethoxyphenyl)amino)methylene)malonate (10 g, 29.3 mmol). The mixture was stirred at the same temperature for 40 mins. LCMS indicated completion of the reaction. The reaction was allowed to cool at rt for 5 mins and was then poured into cold hexane, the yellow precipitate was collected by filtration, washed with hexane and dried in the air. This reaction was carried out in similar scale for several times. From a total of 72 g of diethyl 2-(((2-fluoro-3,4-dimethoxyphenyl)amino)methylene)malonate (211 mmol), ethyl 8-fluoro-6,7-dimethoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate (38 g, 129 mmol, 61.0% yield) was obtained as a yellow solid. LCMS (M+H)+: 296.0

Aufarbeitung

  1. customcompletion of the reaction
  2. filtrationthe yellow precipitate was collected by filtration
  3. washwashed with hexane
  4. customdried in the air

Quellen und Nachweise

ORD-Eintrag
ord-9c8c52ae11254b36a17e745f6d08e698
Quelldatensatz
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09340556B2

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