CH139431A - 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.

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Publication number
CH139431A
CH139431A CH139431DA CH139431A CH 139431 A CH139431 A CH 139431A CH 139431D A CH139431D A CH 139431DA CH 139431 A CH139431 A CH 139431A
Authority
CH
Switzerland
Prior art keywords
acid
preparation
carboxylic acid
petroleum ether
basic derivative
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 CH139431A publication Critical patent/CH139431A/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

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

Description

  

  Verfahren zur Darstellung eines basischen Derivates einer substituierten       Chinolincarbonsäure.       Es wurde gefunden, dass man zu  einem     basischen    Derivat einer     substituierten          Chino-lincarbonsäure    gelang-, wenn man auf       Säurehalogenide    der     2-Halogen-4-chinolincar-          bonsäure        asymmetrisches        Diäthyläthyiendia-          min        einwirken    lässt und das erhaltene 2  Halogen-4-,

  chinolincarbonsäure -     diäthylä@thy-          lendiamid    mit alkalischen     Mitteln,    die zur  Einführung der     Cyclohexyloxygruppe    dienen,  umsetzt.  



  Das     2-Cyclohexyloxy-4-chinolincarbon-          säure-diäthyläthylendiami$    bildet farblose       Kristalle    vom     ,Schmelzpunkt    69  . Die Base ist  in kaltem     Petroläther    schwer löslich; in war  mem     Petroläther,        wie    in den übrigen orga  nischen     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 1,2 Teilen asymme  trischem     Diäthyläthylendiamin    in 45 Teilen    10%     iger        Natronlauge    gibt man unter Küh  lung und     .gändigem    Umrühren allmählich  eine     benzolische    Lösung von 2,2 Teilen     2-          Chlor-4-cIiinolincarbonsäureGhlo,rid    zu. Nach  beendigter Reaktion     wird    die     benzolische    Lö  sung abgetrennt,     ..die    gebildete Base mit Salz  säure ausgezogen und mit Soda wieder aus  gefällt.

   Man     nimmt    die     Base    in Äther auf,       vertreibt    das Lösungsmittel     und    kristallisiert  aus     Petroläther    um.     Dass        2-Chlor-4-chinolin-          carbonsäure-,diäthyläthylendiamidbildet    farb  lose,     blättrige        Kristalle    vom     Schmelzpunkt     74'.

   In den     meisten    organischen     Lösungs-          mitteln    ist die Base     leicht    löslich; mit Säu  ren bildet sie neutrale,     was.serlösliche        Salze.     



  2;6 Teile     Natrium    werden mit 12 Teilen       Cyelo@hexylalkoh.ol    durch Erwärmen in To  luollösung umgesetzt. Hierauf gibt man 30  Teile     2-Chlor-4-cIiinolincarbo@nsäure-diäthyl-          äthylendiamid    hinzu und     erwärmt    im     01bad     bis zur     Beendigung    der Reaktion. Man  wäscht mit Wasser aus und destilliert das       Lösungsmittel    im Vakuum ab. Man erhält      das     2-Cyclohexyloxy-4-chinolincarbonsäure-          diäthylätliylendiamid    als 01, das alsbald zu  farblosen     Kristallen    erstarrt.

   Die Baue lässt  sich aus     Petroläther        umkristallisieren.     



  Zur Einführung der     Cyclohexyloxygruppe          können    .auch andere     Metallcyklohexylate    in  organischen Lösungsmitteln oder zum Bei  spiel     auch        Alkalien    in Gegenwart von     Cyelo-          liexylalkohol        Verwendung    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 quinolinecarboxylic acid is obtained if asymmetric diethylethylenediamine is allowed to act on acid halides of 2-halo-4-quinolinecarboxylic acid and the 2 halo-4-,

  quinoline carboxylic acid - diethylä @ thy- lendiamid with alkaline agents that are used to introduce the cyclohexyloxy group.



  The 2-cyclohexyloxy-4-quinolinecarboxylic acid diethyläthylendiami $ forms colorless crystals with a melting point of 69. The base is sparingly soluble in cold petroleum ether; In war mem petroleum ether, as in the other organic solvents, it is easily soluble. 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 1.2 parts of asymmetric diethylethylenediamine 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 stirring -cIiinolinecarbonsäureGhlo, rid to. After the reaction has ended, the benzene solution is separated off, .. the base formed is extracted with hydrochloric acid and precipitated again with soda.

   The base is taken up in ether, the solvent is driven off and recrystallized from petroleum ether. That 2-chloro-4-quinolinecarboxylic acid, diethylethylenediamide forms colorless, leafy crystals with a melting point of 74 '.

   The base is easily soluble in most organic solvents; with acids it forms neutral, soluble salts.



  2; 6 parts of sodium are reacted with 12 parts of Cyelo@hexylalkoh.ol by heating in a toluene solution. Then 30 parts of 2-chloro-4-quinolinecarbonic acid diethyl ethylenediamide are added and the mixture is heated in the oil bath until the reaction is complete. It is washed with water and the solvent is distilled off in vacuo. The 2-cyclohexyloxy-4-quinolinecarboxylic acid diethylethylenediamide is obtained as 01, which soon solidifies to form colorless crystals.

   The structure can be recrystallized from petroleum ether.



  Other metal cyclohexylates in organic solvents or, for example, alkalis in the presence of cyclohexyl alcohol can also be used to introduce the cyclohexyloxy group.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines basischen Derivates einer substituierten Chinolincarbon- säure, dadurch gekennzeichnet, dass man auf Sä"ureha.logenide der 2-IIalogen-4-chinolinear- bonsäure asymmetrisches Diäthyläthylendiar min einwirken lässt und das erhaltene 2- Ha- loben -4-chinolincarbansäure - diäthyläthylen- diamid mit alkalischen Mitteln, die zur Ein führung der Cyclohexyloxygruppe dienen, umsetzt. PATENT CLAIM: Process for the preparation of a basic derivative of a substituted quinolinecarboxylic acid, characterized in that asymmetric diethylethylenediar is allowed to act on acid allografts of 2-IIalogen-4-quinolinearboxic acid and the 2- Ha- praises -4 -quinoline carbanic acid - diethylethylene diamide with alkaline agents that are used to introduce the cyclohexyloxy group. Das 2-Cycloliexyloxy-4-chinolinearbon- sELure-diäthyliithylendiamid bildet farblose Kristalle vom Schmelzpunkt<B>69'.</B> Die Base ist in kaltem Petroläther schwer löslich; in warmem Petroläther, wie in den übrigen or ganischen Lösungsmitteln ist sie leicht lös lich. Mit Säuren gibt sie neutrale, in Wasser leicht lösliche Salze. Die neue Verbindung soll zu therapeuti schen Zwecken Verwendung finden. 2-Cycloliexyloxy-4-quinolinearbo-acid diethylithylenediamide forms colorless crystals with a melting point of <B> 69 '. </B> The base is sparingly soluble in cold petroleum ether; in warm petroleum ether, as in the other organic solvents, it is easily soluble. With acids it gives neutral, easily soluble salts in water. The new connection is intended to be used for therapeutic purposes.
CH139431D 1927-11-19 1927-11-19 Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. CH139431A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH139431T 1927-11-19
CH137338T 1931-12-21

Publications (1)

Publication Number Publication Date
CH139431A true CH139431A (en) 1930-04-15

Family

ID=25712941

Family Applications (1)

Application Number Title Priority Date Filing Date
CH139431D CH139431A (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) CH139431A (en)

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