CH125409A - Process for the preparation of a substituted quinoline carboxylic acid derivative. - Google Patents

Process for the preparation of a substituted quinoline carboxylic acid derivative.

Info

Publication number
CH125409A
CH125409A CH125409DA CH125409A CH 125409 A CH125409 A CH 125409A CH 125409D A CH125409D A CH 125409DA CH 125409 A CH125409 A CH 125409A
Authority
CH
Switzerland
Prior art keywords
carboxylic acid
preparation
diethylamine
acid derivative
quinoline carboxylic
Prior art date
Application number
Other languages
German (de)
Inventor
Gesellschaft Fuer Chemis Basel
Original Assignee
Chem Ind Basel
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 Chem Ind Basel filed Critical Chem Ind Basel
Publication of CH125409A publication Critical patent/CH125409A/en

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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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Quinoline Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  Verfahren zur Darstellung eines substituierten     Chinolincarbonsäurederivates.       Es wurde gefunden, dass man. zu einem  substituierten     Chinolincarbonsäurederivat    ge  langt, wenn man auf     a-Halogen-;        -chir)olin-          carbonsäurehalogenid        Diäthylamin    einwirken  lässt und das erhaltene     a-Halogen-r-chinolin-          carbonsäure-diäthylamid    mit     Diäthylamin    um  setzt.  



  Das auf diese Weise gewonnene     a-Diäthyl-          amino-r-chinolincarbonsäure-diäthylamid    bil  det ein gelbliches Öl vom     Sdp.        16511    bei  0,02 mm Druck. Es erstarrt nach längerem  Stehen zu fast farblosen     Kristallen    vom       Smp.    76  . In Wasser und in kaltem     Petrol-          ä        ther    ist die Base schwer löslich, in ver  dünnten Säuren, in warmem     Petroläther    so  wie in andern organischen Lösungsmitteln  hingegen leicht löslich. Die Lösungen der  freien Base fluoreszieren blau.

   Das in Alko  hol schwer lösliche     Pikrat    schmilzt bei 178  .  



  Die neue Verbindung soll therapeutische  Verwendung finden.  



       Beispiel:     Eine     benzolische    Lösung von 2,2 Teilen       a-Chlor-r-chinolincarborrsäurechlorid    wird un  ter Kühlung allmählich     reit    1,5 Teilen Di-         äthylamin    versetzt.

   Nach beendeter Reaktion  wird vom abgeschiedenen     Diäthylaminchlor-          hydrat        abfiltriert,    mit Benzol nachgewaschen  und das Lösungsmittel     abdestilliert.        flus    Al  kohol umkristallisiert bildet das     a-Chlor-r-          chinolincarbonsäure-diäthylamid    farblose Kri  stalle vom     Smp.    124  .  



  41,6 Teile     a-Chlor-r-chinolincarbonsäure-          diäthylamid    werden mit 24 Teilen     Diäthyl-          amin    im geschlossenen Gefäss bis zur Been  digung der Reaktion auf 130   erhitzt. Dann  wird mit Äther und Wasser versetzt, abge  trennt und aus der ätherischen Lösung die  Base mit wässeriger Mineralsäure ausgezogen.  Aus der sauren Lösung wird das     a-Diäthyl-          amino-r-chinolincarbonsäure-diäthylarnid    mit  Soda gefällt, auf üblichem Wege isoliert und  aus     Petroläther    umkristallisiert.  



  Die Darstellung gelingt auch in einem  Reaktionsgang durch Umsetzung von     a-Halo-          gen-r-chirrolincarbonsäure-halogenid    mit über  schüssigem     Diäthylamin.  



  Process for the preparation of a substituted quinoline carboxylic acid derivative. It was found that one. to a substituted quinoline carboxylic acid derivative ge reached when one on a-halogen; -chir) olin-carboxylic acid halide diethylamine can act and the a-halo-r-quinoline-carboxylic acid diethylamide obtained is implemented with diethylamine.



  The a-diethylamino-r-quinolinecarboxylic acid diethylamide obtained in this way forms a yellowish oil with bp 16511 at 0.02 mm pressure. After standing for a long time it solidifies to form almost colorless crystals with a melting point of 76. The base is sparingly soluble in water and in cold petroleum ether, but easily soluble in dilute acids, in warm petroleum ether as well as in other organic solvents. The solutions of the free base fluoresce blue.

   Picrate, which is sparingly soluble in alcohol, melts at 178.



  The new compound should find therapeutic use.



       Example: A benzene solution of 2.2 parts of a-chloro-r-quinolinecarboric acid chloride is gradually admixed with 1.5 parts of diethylamine under cooling.

   After the reaction has ended, the precipitated diethylamine chlorohydrate is filtered off, washed with benzene and the solvent is distilled off. Recrystallized from flux alcohol, the a-chloro-r-quinolinecarboxylic acid diethylamide forms colorless crystals with a melting point of 124.



  41.6 parts of a-chloro-r-quinolincarboxylic acid diethylamide are heated to 130 with 24 parts of diethylamine in a closed vessel until the reaction has ended. Ether and water are then added, the mixture is separated off and the base is extracted from the ethereal solution with aqueous mineral acid. The a-diethylamino-r-quinolinecarboxylic acid diethyl amide is precipitated from the acidic solution with soda, isolated in the usual way and recrystallized from petroleum ether.



  The preparation is also possible in one reaction step by reacting α-halogen-r-chirroline carboxylic acid halide with excess diethylamine.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines substitu ierten Chinolincarbonsäurederivates, dadurch gekennzeichnet; dass man a-11alogeu-r-cliino- lincarbonsäurehalogenid Diäthylamin einwir ken lässt und das erhaltene a-Halogen-r-chi- nolincai'bonsäui,e-diäthylamid mit Diäthylamin umsetzt. Das auf diese Weise gewonnene a-Diäthyl- amino-r-chinolincarbonsäure-diäthylamid bil det ein gelbliches 01 vom Sdp. 165 bei 0,02 mm Druck. PATENT CLAIM: Process for the preparation of a substituted quinoline carboxylic acid derivative, characterized; that a-11alogeu-r-cliino-lincarboxylic acid halide diethylamine is allowed to act and the a-halogen-r-quinoline-lincai'bonsäui, e-diethylamide obtained are reacted with diethylamine. The a-diethylamino-r-quinolinecarboxylic acid diethylamide obtained in this way forms a yellowish oil with a bp 165 at 0.02 mm pressure. Es erstarrt nach längerem Stehen zu fast farblosen Kristallen vom Smp. 76 . In Wasser und in kaltem Petrol- äther ist die 13ase schwer löslich, in verdünn ten Säuren, in warmem Petroläther sowie in andern organischen Lösungsmitteln hingegen leicht löslich. Die Lösungen der freien Base fluoreszieren blau. Das in Alkohol schwer lösliche Pikrat schmilzt bei 178 . Die neue Verbindung soll therapeutische Verwendung finden. After standing for a long time it solidifies to form almost colorless crystals with a melting point of 76. 13ase is sparingly soluble in water and cold petroleum ether, but easily soluble in dilute acids, warm petroleum ether and other organic solvents. The solutions of the free base fluoresce blue. Picrate, which is sparingly soluble in alcohol, melts at 178. The new compound should find therapeutic use.
CH125409D 1926-04-30 1926-04-30 Process for the preparation of a substituted quinoline carboxylic acid derivative. CH125409A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH125409T 1926-04-30
CH124228T 1929-04-17

Publications (1)

Publication Number Publication Date
CH125409A true CH125409A (en) 1928-04-16

Family

ID=25710216

Family Applications (1)

Application Number Title Priority Date Filing Date
CH125409D CH125409A (en) 1926-04-30 1926-04-30 Process for the preparation of a substituted quinoline carboxylic acid derivative.

Country Status (1)

Country Link
CH (1) CH125409A (en)

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