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DE668742C - Process for the preparation of 2-phenylquinoline-4-carboxylic acids containing iodine and oxy groups - Google Patents

Process for the preparation of 2-phenylquinoline-4-carboxylic acids containing iodine and oxy groups

Info

Publication number
DE668742C
DE668742C DESCH112163D DESC112163D DE668742C DE 668742 C DE668742 C DE 668742C DE SCH112163 D DESCH112163 D DE SCH112163D DE SC112163 D DESC112163 D DE SC112163D DE 668742 C DE668742 C DE 668742C
Authority
DE
Germany
Prior art keywords
preparation
phenylquinoline
carboxylic acids
oxy groups
acids containing
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
DESCH112163D
Other languages
German (de)
Inventor
Dr Paul Diedrich
Dr Max Dohrn
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer Pharma AG
Original Assignee
Schering AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Schering AG filed Critical Schering AG
Priority to DESCH112163D priority Critical patent/DE668742C/en
Application granted granted Critical
Publication of DE668742C publication Critical patent/DE668742C/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D215/50—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4
    • C07D215/52—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4 with aryl radicals attached in position 2

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Verfahren zur Darstellung von Jod und Oxygruppen enthaltenden 2-Phenylchinolin-4-carbonsäuren Gegenstand des Patents 659 496 ist ein; Verfahren zur Darstellung von jodierten Oxyabkömmlingen der a-Phenylchinolincarbonsäure, -das darin besteht, daß man 3, 5-DZ-jod-4-oxyacetophenon sowie seine in der Hydroxylgruppe verätherten Abkömmlinge mit Isatinen kondensiert. Diese Kondensationen verlaufen meistens in der Weise, daß aus den, Ausgangsstoffen unmittelbar das Endprodukt entsteht. Es besteht aber auch die Möglich- keit, daß zunächst ein Zwischenprodukt und im weiteren Verlauf des Verfahrens aus diesem durch Umlagerung erst das Endprodukt gebildet wird. Ein solcher Fall liegt z. B. bei der Herstellung der nach Beispiel 5 des Hauptpatents erhabenen 2-(3', 5'-DijOd-4'-oxyz' - ß - oxäthylphenyl) - 6 - jodchinolin - 4 - carbonsäure vor, bei welcher die Umsetzung in folgender Weise verläuft: Es wurde nun gefunden, daß man bei der Herstellung solcher Verbindungen zu bedeutend höheren Ausbeuten gelangt, wenn man die Kondensation nicht in einer Stufe, mäß dem Verfahren des Hauptpatents, s , dern in zwei Stufen unter Abtrennung erhaltenen Zwischenprodukts ausführt. S10 #e3, hält man bei Anwendung des zweistufigeü'Verfahrens bei der nach Beispiel 5 des Hauptpatents ausgeführten Kondensation eine gegenüber dem einstufigen Verfahren um über I oo ö/o gesteigerte Ausbeute.Process for the preparation of 2-phenylquinoline-4-carboxylic acids containing iodine and oxy groups The subject of patent 659 496 is a; Process for the preparation of iodinated oxy derivatives of α-phenylquinoline carboxylic acid, which consists in condensing 3, 5-DZ-iodo-4-oxyacetophenone and its derivatives etherified in the hydroxyl group with isatins. These condensations usually take place in such a way that the end product is created directly from the starting materials. But there is also the possibility The fact that an intermediate product is initially formed and, in the further course of the process, the end product is only formed from this by rearrangement. Such a case is e.g. B. in the preparation of the raised according to Example 5 of the main patent 2- (3 ', 5'-DijOd-4'-oxyz' - ß - oxäthylphenyl) - 6 - iodoquinoline - 4 - carboxylic acid, in which the reaction in the following way It has now been found that, in the preparation of such compounds, significantly higher yields are obtained if the condensation is not carried out in one stage, in accordance with the process of the main patent, in which the intermediate product obtained is separated off in two stages. S10 # e3, when the two-stage process is used in the condensation carried out according to Example 5 of the main patent, a yield that is over 100% higher than in the one-stage process is maintained.

Beispiel 27,39 5-Jodisatin und 43,29 3, 5-Dijod-4-oxyäthoxyacetophenon werden mit 3o ccm 3:3 %iger Kalilauge und I oo ccm Wasser etwa r Stunde zum Sieden erhitzt, das Umsetzungsgemisch mit Wasser verdünnt .und mit verdünnter Salzsäure in der Hitze gefällt. Das erhaltene, dem Endprodukt isomere Zwischenprodukt zeigt einen Zersetzungspunkt von etwa 270'. Es wird zwecks Umlagerng in das wirksame Endprodukt mit 6o ccm 33 o/oigex Kalilauge und I 2o ccm Alkohol 5 Stunden zum Sieden erhitzt und das Umsetzungsgut `.mach dem Verfahren des Hauptpatents aufrb@eitet. Das hellbraune Endprodukt hat nselben Zersetzungspunkt von 242 bis 245° ,n das im Einstufenverfahren erhaltene: Aus-'beute 8o% der Theorie.Example 27,39 5-iodisatin and 43,29 3,5-diiodo-4-oxyethoxyacetophenone are heated to boiling with 3o ccm 3: 3% potassium hydroxide solution and 10o ccm water for about 1 hour, the reaction mixture is diluted with water and with diluted hydrochloric acid precipitated in the heat. The intermediate product obtained, isomeric to the end product, has a decomposition point of about 270 °. For the purpose of rearrangement into the effective end product, it is heated to boiling for 5 hours with 6o ccm 33% potassium hydroxide solution and 12o ccm alcohol and the reaction material is prepared according to the process of the main patent. The light brown end product has the same decomposition point of 242 to 245 °, the one obtained in the one-step process: Yield 80% of theory.

Claims (1)

PATI:NTANSPIZUCII: Verfahren zur Darstellung von Jod und Oxygruppen enthaltenden 2-Phenylchinolin-4#carbonsäuren, dadurch gekennzeichnet, daß man in weiterer Ausbildung des Verfahrens des Patents 659 4.96 in der Hydroxylgruppie verätherte Abkömmlinge von 3, 5-Dijod-4-oxyacetophenon mit 5-Jodisatin in alkalischer Lösung kondensiert und das entstandene Kondensationsprodukt in alkoholisch-,alkalischer Lösung der Einwirkung von Umlagerungsmitteln unterwirft.PATI: NTANSPIZUCII: Process for the preparation of iodine and oxy groups containing 2-phenylquinoline-4 # carboxylic acids, characterized in that in further development of the process of patent 659 4.96 etherified in the hydroxyl group Derivatives of 3, 5-diiodo-4-oxyacetophenone with 5-iodisatin in alkaline solution condensed and the resulting condensation product in alcoholic, alkaline Solution subjected to the action of rearrangement agents.
DESCH112163D 1936-05-26 1936-05-26 Process for the preparation of 2-phenylquinoline-4-carboxylic acids containing iodine and oxy groups Expired DE668742C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DESCH112163D DE668742C (en) 1936-05-26 1936-05-26 Process for the preparation of 2-phenylquinoline-4-carboxylic acids containing iodine and oxy groups

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DESCH112163D DE668742C (en) 1936-05-26 1936-05-26 Process for the preparation of 2-phenylquinoline-4-carboxylic acids containing iodine and oxy groups

Publications (1)

Publication Number Publication Date
DE668742C true DE668742C (en) 1941-06-27

Family

ID=7449559

Family Applications (1)

Application Number Title Priority Date Filing Date
DESCH112163D Expired DE668742C (en) 1936-05-26 1936-05-26 Process for the preparation of 2-phenylquinoline-4-carboxylic acids containing iodine and oxy groups

Country Status (1)

Country Link
DE (1) DE668742C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4680299A (en) * 1984-04-30 1987-07-14 E.I. Du Pont De Nemours And Company 2-phenyl-4-quinolinecarboxylic acids and pharmaceutical compositions thereof

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4680299A (en) * 1984-04-30 1987-07-14 E.I. Du Pont De Nemours And Company 2-phenyl-4-quinolinecarboxylic acids and pharmaceutical compositions thereof

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