DE373285C - Process for the preparation of a 2-phenylquinolinedicarboxylic acid - Google Patents

Process for the preparation of a 2-phenylquinolinedicarboxylic acid

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Publication number
DE373285C
DE373285C DEN16994D DEN0016994D DE373285C DE 373285 C DE373285 C DE 373285C DE N16994 D DEN16994 D DE N16994D DE N0016994 D DEN0016994 D DE N0016994D DE 373285 C DE373285 C DE 373285C
Authority
DE
Germany
Prior art keywords
acid
phenylquinolinedicarboxylic
preparation
acetophenone
phenylquinoline
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
DEN16994D
Other languages
German (de)
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.)
Neumann & Co Dr GmbH
Original Assignee
Neumann & Co Dr GmbH
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 Neumann & Co Dr GmbH filed Critical Neumann & Co Dr GmbH
Priority to DEN16994D priority Critical patent/DE373285C/en
Application granted granted Critical
Publication of DE373285C publication Critical patent/DE373285C/en
Expired legal-status Critical Current

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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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

Verfahren zur Herstellung einer 2-Phenylchinolindicarbonsäure. Bei Einwirkung von Acetophenon auf Isatin in Gegenwart von überschüssigem Alkali in alkoholischer Lösung erhält man bekanntlich 2-Phenylchinolin-4-oarbonsäure. Die bekannten therapeutischen Eigenschaften -dieser Säure werden jedoch stark durch Nebenwirkungen sowie durch schlechten Geschmack beeinträchtigt.Process for the preparation of a 2-phenylquinolinedicarboxylic acid. at Action of acetophenone on isatin in the presence of excess alkali in As is known, 2-phenylquinoline-4-carboxylic acid is obtained in alcoholic solution. the Known therapeutic properties -this acid, however, are strongly influenced by Side effects as well as impaired by bad taste.

Es hat sich nun herausgestellt, daß durch Einführung einer weiteren Carboxylgruppe in das Molekyl der 2-Phenylchinolin-4-carbonsäure die therapeutischen Eigenschaften der Säure wesentlich verändert werden. Die Einführung der Carboxylgruppe wird dadurch bewirkt, @daß man an Stelle des Acetophenon die Acetophenon-o-oarbonsäure mit Isatin in alkalischer Lösung kondensiert. Beispiel.It has now been found that introducing a further carboxyl group into the molecule of 2-phenylquinoline-4-carboxylic acid significantly changes the therapeutic properties of the acid. The introduction of the carboxyl group is brought about by using the acetophenone-o-carboxylic acid instead of the acetophenone condensed with isatin in alkaline solution. Example.

Ein Mol. Acetophenon-o-carbon@säure (hergestellt aus Phtalsäureanhydrid, Essigsäureanhydrid und Kaliumacetat) wird mit einem Mol.Isatin in einem großen Überschuß von 33prozentiger wäßriger Kalilauge gelöst und auf dem Wasserbade erhitzt. Nach q. Stunden fällt man die entstandene 2-Phenylchinolind. # 2'@dicarbonsäure mit Essigsäure aus. Nach mehrmaligem Umkristallisieren aus Wasser erhält man sie in Form eines schwach gelblichen Pulvers von säuerlichem Geschmack.One mole of acetophenone-o-carboxylic acid (made from phthalic anhydride, Acetic anhydride and potassium acetate) is used with a mol.Isatin in a large excess dissolved by 33 percent aqueous potassium hydroxide solution and heated on the water bath. To q. The 2-phenylquinoline formed is precipitated for hours. # 2 '@ dicarboxylic acid with acetic acid the end. After repeated recrystallization from water, it is obtained in the form of a slightly yellowish powder with a sour taste.

Der Schmelzpunkt liegt bei 2oo°.The melting point is 200 °.

Das so -gewonnene Produkt ist schwer löslich in Alkohol, Aether und Chloroform, leichter löslich in Essigsäureaethylester. Seine Alkalisalze sind sämtlich leicht wasserlöslich, charakteristisch ist das wasserlösliche, gut-kristallisierende Calciumsalz.The product thus obtained is sparingly soluble in alcohol, ether and Chloroform, more readily soluble in ethyl acetate. Its alkali salts are all Easily soluble in water, characteristic is the water-soluble, well-crystallizing Calcium salt.

Es sind bereits Isomere,der gemäß vorliegendem Verfahren (darstellbaren Phenylchinolindicarbonsäure bekannt. - Die aus Acetophenon-o-carbonsäure hergestellte 2-Phenylchinolin-q. # 2'-dicarbontsäure besitzt nun wertvolle physiologische Eigenschaften, die den Isomeren nicht zukommen, sie beeinflußt nämlich 'den P!urinstoffwechsel stark.There are already isomers that can be represented according to the present process Phenylquinolinedicarboxylic acid known. - The one made from acetophenone-o-carboxylic acid 2-phenylquinoline-q. # 2'-dicarboxylic acid now has valuable physiological properties, which are not attributable to the isomers, namely it influences the purine metabolism strong.

Von der 4-Monocarbonsäure unterscheidet sich die neue Säure einerseits durch bedeutend besseren Geschmack, arndererseits,dad'urch"daß sie, wie vergleichende Versuche ergeben haben, nicht nur eine starke Vermehrung der Harnsäureausfuhr, sondern auch der Vorstufe der Harnsäure, der Purinbasen, aus dem Körper herbeiführt.On the one hand, the new acid differs from the 4-monocarboxylic acid by significantly better taste, on the other hand, by the fact that they are like comparative Experiments have shown not only a strong increase in uric acid export, but also brings about the preliminary stage of uric acid, the purine bases, from the body.

Claims (1)

PATENTANSPRUCH Verfahren zur Herstellung einer 2-Phenylchinolin)dicarbonsäure, dadurch gekennzeichnet, daß man Acetophenon-o-carbonsäure mit Isatin in Gegenwart von Alkali kondensiert.PATENT CLAIM Process for the production of a 2-phenylquinoline) dicarboxylic acid, characterized in that acetophenone-o-carboxylic acid is used with isatin in the presence condensed by alkali.
DEN16994D 1917-10-14 1917-10-14 Process for the preparation of a 2-phenylquinolinedicarboxylic acid Expired DE373285C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEN16994D DE373285C (en) 1917-10-14 1917-10-14 Process for the preparation of a 2-phenylquinolinedicarboxylic acid

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEN16994D DE373285C (en) 1917-10-14 1917-10-14 Process for the preparation of a 2-phenylquinolinedicarboxylic acid

Publications (1)

Publication Number Publication Date
DE373285C true DE373285C (en) 1923-04-10

Family

ID=7340308

Family Applications (1)

Application Number Title Priority Date Filing Date
DEN16994D Expired DE373285C (en) 1917-10-14 1917-10-14 Process for the preparation of a 2-phenylquinolinedicarboxylic acid

Country Status (1)

Country Link
DE (1) DE373285C (en)

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