CH139446A - 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
CH139446A
CH139446A CH139446DA CH139446A CH 139446 A CH139446 A CH 139446A CH 139446D A CH139446D A CH 139446DA CH 139446 A CH139446 A CH 139446A
Authority
CH
Switzerland
Prior art keywords
carboxylic acid
acid
preparation
quinoline carboxylic
diethylpropylenediamide
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 CH139446A publication Critical patent/CH139446A/en

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D215/00Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02Heterocyclic 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
    • C07D215/16Heterocyclic 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
    • C07D215/48Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D215/50Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4

Description

  

  Verfahren zur Darstellung eines Basisehen Derivates einer substituierten       Chinolincarbonsäure.       Es wurde gefunden, dass man zu einem  basischen Derivat einer substituierten     Chino-          lincarbonsäure    gelangt, wenn man auf Säure  halogenide der     2-Halogen-4-ehinolincarbon-          säure        Diäthylpropylendiämin    der Formel  
EMI0001.0007     
    einwirken lässt und das erhaltene     2-Halogen-          4    -     chinolincarbonsäure    -     diäthylpropylendiamid     mit alkalischen     Äthogylierungsmitteln    um  setzt.  



  Das     2-Äthogy-4-chinolincarbonsäure-di-          äthylpropylendiamid    bildet farblose Kristalle  vom Schmelzpunkt 740. Die Base ist in  kaltem     Petroläther    schwer löslich; in warmem       Petroläther,    wie in den übrigen organischen  Lösungsmitteln ist sie leicht löslich.     Mit     Säuren gibt sie neutrale, in Wasser leicht  lösliche Salze.  



  Die neue Verbindung soll zu therapeuti  schen Zwecken Verwendung finden.    <I>Beispiel:</I>  Zu einer Lösung von 1,3 Teilen     Diäthyl-          propylendiamin    in 45 Teilen 10     %iger    Natron  lauge gibt man unter Kühlung und ständigem  Umrühren allmählich eine     benzolische    Lösung  von 2,2 Teilen     2-Chlor-4-chinolinoarbonsäure-          chlorid    zu. Nach beendigter Reaktion wird  die     benzolische    Lösung abgetrennt, die ge  bildete Base mit Salzsäure ausgezogen und  mit Soda wieder ausgefällt. Man nimmt die  Base in Äther auf, vertreibt das Lösungs  mittel und kristallisiert sie aus     Petroläther     um.

   Das     2-Chlor-4-chinolincarbonsäure-diäthyl-          propylendiamid    bildet farblose, blätterige Kri  stalle vom Schmelzpunkt 66 0. In den meisten  organischen Lösungsmitteln ist die Base leicht  löslich; mit Säuren bildet sie neutrale, wasser  lösliche Salze.  



  Das asymmetrische     Diäthylpropylendiamin     (Siedepunkt 162 0) wird bei der Reduktion  von     Diäthylaminopropionitril    mit Natrium  und     Alkohol    erhalten. Das     Nitril        (Sdp.    20      80      )    bildet sich bei der     Kondensation    von       Acetaldehyd    mit Blausäure und     Diäthylamin.     



  32 Teile     2-Chlor-4-chinolincarbonsäure-          diäthylpropylendiamid    werden mit einer Lö  sung von 2,6 Teilen Natrium in Äthylalkohol  gekocht. Hierauf wird der Äthylalkohol ab  destilliert, der Rückstand in Äther aufge  nommen und mit Wasser gewaschen. Nach  Entfernung des Lösungsmittels verbleibt das       2-Äthoxy-4-chinolincarbonsäLlre-diäthylpropy-          lendiamid    als farblose Kristalle, die aus     Pe-          troläther    umkristallisiert werden können.  



  Zur Einführung der     Äthoxygruppe    können  auch andere     Metalläthylate    in organischen  Lösungsmitteln oder zum Beispiel auch     Al-          kalien    in Gegenwart von Äthylalkohol Ver  wendung finden.



  Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. It has been found that a basic derivative of a substituted quinoline carboxylic acid is obtained when acid halides of the 2-halo-4-ehinoline carboxylic acid diethylpropylenediamine of the formula are used
EMI0001.0007
    can act and the resulting 2-halo 4 - quinoline carboxylic acid - diethylpropylenediamide with alkaline ethogylating agents.



  The 2-ethogy-4-quinolinecarboxylic acid diethylpropylenediamide forms colorless crystals with a melting point of 740. The base is sparingly soluble in cold petroleum ether; It is easily soluble in warm petroleum ether, as in the other 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 1.3 parts of diethylpropylenediamine in 45 parts of 10% sodium hydroxide solution, a benzene solution of 2.2 parts of 2-chloro-4- is gradually added with cooling and constant stirring quinolinoarboxylic acid chloride to. After the reaction has ended, the benzene solution is separated off, the base formed is extracted with hydrochloric acid and reprecipitated with soda. The base is taken up in ether, the solvent is driven off and it is recrystallized from petroleum ether.

   The 2-chloro-4-quinolinecarboxylic acid diethylpropylenediamide forms colorless, leafy crystals with a melting point of 66 0. The base is easily soluble in most organic solvents; with acids it forms neutral, water-soluble salts.



  The asymmetrical diethylpropylenediamine (boiling point 162 0) is obtained in the reduction of diethylaminopropionitrile with sodium and alcohol. The nitrile (bp. 20 80) is formed during the condensation of acetaldehyde with hydrocyanic acid and diethylamine.



  32 parts of 2-chloro-4-quinolincarboxylic acid diethylpropylenediamide are boiled with a solution of 2.6 parts of sodium in ethyl alcohol. Then the ethyl alcohol is distilled off, the residue taken up in ether and washed with water. After the solvent has been removed, the 2-ethoxy-4-quinoline-carboxylic acid diethylpropylene diamide remains as colorless crystals which can be recrystallized from petroleum ether.



  Other metal ethylates in organic solvents or, for example, alkalis in the presence of ethyl alcohol can also be used to introduce the ethoxy group.

 

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines basischen Derivates einer substituierten Chinolincarbon- säure, dadurch gekennzeichnet, dass man auf Säurehalogenide der 2-Halogen-4-chinolincar- bonsäure Diäthylpropylendiamin der Formel EMI0002.0022 einwirken lässt und das erhaltene 2-Halogen- 4 - chinolincarbonsäure - diäthylpropylendiamid mit alkalischen Äthoxylierungsmitteln um setzt. PATENT CLAIM: Process for the preparation of a basic derivative of a substituted quinolinecarboxylic acid, characterized in that acid halides of 2-halo-4-quinolinecarboxylic acid are diethylpropylenediamine of the formula EMI0002.0022 can act and the resulting 2-halo-4 - quinoline carboxylic acid - diethylpropylenediamide with alkaline ethoxylating agents to implement. Das 2-Äthoxy-4-chinolincarbonsäure-di- äthylpropylendiamid bildet farblose Kristalle vom Schmelzpunkt 740. Die Base ist in kaltem Petroläther schwer löslich; in warmem Petroläther, wie in den übrigen organischen Lösungsmitteln ist sie leicht löslich. Mit Säuren gibt sie neutrale, in Wasser leicht lösliche Salze. Die neue Verbindung soll zu therapeu tischen Zwecken Verwendung finden. The 2-ethoxy-4-quinolinecarboxylic acid diethylpropylenediamide forms colorless crystals with a melting point of 740. The base is sparingly soluble in cold petroleum ether; It is easily soluble in warm petroleum ether, as in the other organic solvents. With acids it gives neutral, easily soluble salts in water. The new connection is intended to be used for therapeutic purposes.
CH139446D 1927-11-19 1927-11-19 Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. CH139446A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH139446T 1927-11-19
CH137338T 1931-12-21

Publications (1)

Publication Number Publication Date
CH139446A true CH139446A (en) 1930-04-15

Family

ID=25712956

Family Applications (1)

Application Number Title Priority Date Filing Date
CH139446D CH139446A (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) CH139446A (en)

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