StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Malonate Ion → Ethyl 7-fluoro-5,6-dimethoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate

HRID 525934
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 525934
C1C=CC(C2C=CC=CC=2)=CC=1.C1C=CC(OC2C=CC=CC=2)=CC=1.[F:26][C:27]1[CH:28]=[C:29]([NH:37][CH:38]=[C:39]([C:45]([O:47]CC)=O)[C:40]([O:42][CH2:43][CH3:44])=[O:41])[CH:30]=[C:31]([O:35][CH3:36])[C:32]=1[O:33][CH3:34].C([O-])(=O)CC([O-])=O.FC1C(OC)=C(OC)C=C2C=1C(=O)C(C(OCC)=O)=CN2>CCCCCC>[F:26][C:27]1[CH:28]=[C:29]2[C:30]([C:45](=[O:47])[C:39]([C:40]([O:42][CH2:43][CH3:44])=[O:41])=[CH:38][NH:37]2)=[C:31]([O:35][CH3:36])[C:32]=1[O:33][CH3:34]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 9084Malonate IonHCID 246701,1'-Biphenyl, mixt. with 1,1'-oxybis(benzene)HCID 86732800Diethyl 2-(((3-fluoro-4,5-dimethoxyphenyl)amino)methylene)malonateHCID 86732802Ethyl 5-fluoro-6,7-dimethoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate

Produkt 1

HCID 86732801Ethyl 7-fluoro-5,6-dimethoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate
Ausbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
250 °C

Versuchsvorschrift

To Dowtherm (150 mL) heated at 250° C. was added diethyl 2-(((3-fluoro-4,5-dimethoxyphenyl)amino)methylene)malonate (30 g, 87 mmol). The mixture was stirred at 250° C. for 30 min. LCMS indicated completion of the reaction. The reaction mixture was allowed to cool a bit and was then added to cold hexane, the precipitates were collected by filtration, washed with hexane and then allowed to dry in the air. Similar scale reactions were repeated several times. From a total amount of the malonate (148 g, 434 mmol), a mixture of ethyl 5-fluoro-6,7-dimethoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate and ethyl 7-fluoro-5,6-dimethoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate was obtained as brown solid without further purification (103 g, 349 mmol, 80% yield). LCMS: (M+H)+: 296.1.

Aufarbeitung

  1. customcompletion of the reaction
  2. temperatureto cool a bit
  3. filtrationthe precipitates were collected by filtration
  4. washwashed with hexane
  5. customto dry in the air

Quellen und Nachweise

ORD-Eintrag
ord-e3d1f5c85dcb44d7a8c071f54d74ad8e
Quelldatensatz
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09340556B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion