CH139433A - Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. - Google Patents

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

Info

Publication number
CH139433A
CH139433A CH139433DA CH139433A CH 139433 A CH139433 A CH 139433A CH 139433D A CH139433D A CH 139433DA CH 139433 A CH139433 A CH 139433A
Authority
CH
Switzerland
Prior art keywords
preparation
acid
carboxylic acid
basic derivative
quinolinecarboxylic acid
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 CH139433A publication Critical patent/CH139433A/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)
  • Quinoline Compounds (AREA)

Description

  

  Verfahren zur Darstellung eines basischen Derivates einer substituierten       Chinolinearbonsäure.       Es wurde gefunden, dass man zu  einem basischen Derivat einer substituierten       Chinolinearbonsäure    gelangt, wenn man auf       Säurehalogenide    der     2-Halogen-4-chinolincar-          bonsäure        Triäthyläthylendiamin    einwirken  lässt und das erhaltene     2-Halogen-4-chinolin-          carbonsäure-triäthyläthylend'iamid        mit    alkali  schen     Athoxylierungsmitteln    umsetzt.  



  Das     2-Äthogy-4-chinolincarbonsäure-tri-          äthyläthylendiamid    bildet ein hellgelbes     @01     vom Siedepunkt     158-1.60'        bei    0,02 mm       Druck.    Die Base ist     in;    organischen Lösungs  mitteln leicht löslich. Mit Säuren gibt sie neu  trale, in Wasser leicht lösliche Salze.  



  Die neue Verbindung soll zu therapeuti  schen     Zwecken    Verwendung finden.  <I>Beispiel:</I>       .Zu    einer     Lösung    von 1,5 Teilen     Triä-          thyläthylendiamin    (farblose Base vom     Sdp.     <B>160</B> bis     1.65',    dargestellt durch Reduktion  des Kondensationsproduktes aus     as.    Diäthyl-         äthylendiamin    und     Acetaldehyd    vom Siede  punkt 40   bei 7 mm Druck) in 4 Teilen  10 %     iger    Natronlauge lässt man unter Rüh  ren und Kühlen eine     benzolische    Lösung  von 2,

  2 Teilen     2-Chlor-4-ehinolincarbonsäure-          chlorid    allmählich zufliessen. Nach beende  ter Reaktion wird mit Wasser     gewaschen     und das     Lösungsmittel        abdestilliert.    Das     2-          Chlor-4-chinolincarbonsäure    -     triäthyläthy        len-          diamid    bildet ein gelbliches 01 vom Siede  punkt 165   bei     etwa    0,015 mm Druck. In  organischen     Lösungsmitteln    ist es leicht lös  lich. Mit Säure gibt die Base neutrale, was  serlösliche Salze.  



  15 Teile     2-Chlor-4-chino-Iinearbonsäure-          triäthyläthylen.diamid    werden mit einer Lö  sung von 2 Teilen     Natriumhydraxyd        in          4thyla,lliahol    gekocht. Hierauf wird der       Äthylalkohol        abdestilliert,    der Rückstand in  Äther     aufgenommen    und     mit    Wasser gewa  schen. Nach Entfernung     des    Lösungsmittels       verbleibt    das .2-Äahogy-4-chix@olin@arbo@säure-           triäthyläthylendia.mid    als hellgelbes 01. Die  Base lässt sich im Vakuum destillieren.  



  An Stelle einer Lösung von     AlkaIihydro-          xyd    in Äthylalkohol können auch andere  alkalische     Ahoxylierungsmittel        Verwendung     finden, zum Beispiel     Meta.lläthylate    in orga  nischen     Lösungsmitteln.  



  Process for the preparation of a basic derivative of a substituted quinolinearboxylic acid. It has been found that a basic derivative of a substituted quinolinearboxylic acid is obtained if triethylethylenediamine is allowed to act on acid halides of 2-halo-4-quinolinecarboxylic acid and the 2-halo-4-quinolinecarboxylic acid-triäthyläthylend'iamid obtained with alkali between ethoxylating agents.



  The 2-Äthogy-4-quinolinecarboxylic acid tri-ethylethylenediamide forms a light yellow @ 01 with a boiling point of 158-1.60 'at 0.02 mm pressure. The base is in; Easily soluble in organic solvents. With acids it gives neutral, easily soluble salts in water.



  The new connection is intended to be used for therapeutic purposes. <I> Example: </I>. To a solution of 1.5 parts of triethylethylenediamine (colorless base with bp 160 to 1.65 ', produced by reducing the condensation product of as. Diethylethylenediamine and acetaldehyde with a boiling point of 40 at 7 mm pressure) in 4 parts of 10% sodium hydroxide solution, while stirring and cooling, a benzene solution of 2,

  Gradually flow in 2 parts of 2-chloro-4-ehinolincarboxylic acid chloride. When the reaction has ended, the mixture is washed with water and the solvent is distilled off. The 2-chloro-4-quinolinecarboxylic acid - triäthyläthylen- diamid forms a yellowish oil with a boiling point of 165 at about 0.015 mm pressure. It is easily soluble in organic solvents. With acid, the base gives neutral, water-soluble salts.



  15 parts of 2-chloro-4-quino-Iinearbonsäure- triäthyläthylen.diamid are boiled with a solution of 2 parts of sodium hydroxide in 4thyla, lliahol. The ethyl alcohol is then distilled off, the residue is taken up in ether and washed with water. After removing the solvent, the .2-Äahogy-4-chix @ olin @ arbo @ säure- triäthyläthylendia.mid remains as a light yellow 01. The base can be distilled in vacuo.



  Instead of a solution of alkali hydroxide in ethyl alcohol, other alkaline aoxylating agents can also be used, for example Meta.lläthylate in organic solvents.

Claims (1)

<B>PATENTANSPRUCH:</B> Verfahren zur Darstellung eines basischen Derivates einer substituierten Chinolincarbon- säure, dadurch gekennzeichnet, dass man auf Säurehalogenide der 2-Halogen-4-chinolin- carbonsäure-triäthyläthylendiamin einwirken lässt und das erhaltene 2-Halogen-4-chino.Iin- carbonsäure-tizäthylätliylendiamid mit alkali schen Äthoxylierungsmitteln umsetzt. <B> PATENT CLAIM: </B> Process for the preparation of a basic derivative of a substituted quinolinecarboxylic acid, characterized in that acid halides of 2-halo-4-quinolinecarboxylic acid triethylethylenediamine are allowed to act and the 2-halo-4 -chino.Iin- carboxylic acid-tizäthylätliylenediamid with alkaline ethoxylating agents. Das 2-Äthoxy-4-chinolincarbonsäure-tiiä- thyläthylendiamid bildet ein hellgelbes 01 vom Siedepunkt 158 bis <B>160'</B> bei 0,02 mm Druck. Die Base ist in organischen Lösungs mitteln leicht löslich. Mit Säuren gibt sie neu trale, in Wasser leicht lösliche Salze. Die neue Verbindung soll zu therapeuti schen Zwecken Verwendung finden. The 2-ethoxy-4-quinolinecarboxylic acid-thyläthylendiamid forms a light yellow oil with a boiling point 158 to 160 'at 0.02 mm pressure. The base is easily soluble in organic solvents. With acids it gives neutral, easily soluble salts in water. The new connection is intended to be used for therapeutic purposes.
CH139433D 1927-11-19 1927-11-19 Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. CH139433A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH139433T 1927-11-19
CH137338T 1931-12-21

Publications (1)

Publication Number Publication Date
CH139433A true CH139433A (en) 1930-04-15

Family

ID=25712943

Family Applications (1)

Application Number Title Priority Date Filing Date
CH139433D CH139433A (en) 1927-11-19 1927-11-19 Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid.

Country Status (1)

Country Link
CH (1) CH139433A (en)

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