CH139429A - 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
CH139429A
CH139429A CH139429DA CH139429A CH 139429 A CH139429 A CH 139429A CH 139429D A CH139429D A CH 139429DA CH 139429 A CH139429 A CH 139429A
Authority
CH
Switzerland
Prior art keywords
acid
carboxylic acid
preparation
petroleum ether
phenethoxy
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 CH139429A publication Critical patent/CH139429A/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)
  • Plural Heterocyclic Compounds (AREA)

Description

  

      Verfahren    zur Darstellung eines basischen Derivates einer substituierten       Chinolincarbonsäur    e.    Es wurde gefunden, dass man zu  einem basischen Derivat einer substituierten       Chinolincarbonsäure    gelangt,

   wenn man auf       Säurehalogenide    der     2-Halogen-4-chinolincar-          bonsäure    asymmetrisches     Diäthyläthylendia-          min    einwirken lässt und     das    erhaltene     2-          Halogen    - 4 -     chinolincarbonsäure    -     diäthyläthy-          lendiamid    mit alkalischen Mitteln, die zur  Einführung der     Phenäthoxygruppe    dienen,  umsetzt.  



  Das     2-Phenäthoxy-4-chinolincarbonsäure-          diäthyläthylendiamid    bildet farblose Kri  stalle vom     Schmelzpunkt   <B>90'.</B> Die Base ist  in kaltem     Petroläther    schwer löslich; in war  mem     Petroläther,    wie in den übrigen organi  schen     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>       7u    einer     Lösung    von 1,2 Teilen asymme  trischem     Diäthyläthylendiamin    in 45 Teilen         10%        iger    Natronlauge gibt man unter Küh  lung und     @tändi,gem    Umrühren allmählich  eine     benzolische    Lösung von 2,2 Teilen     2-          Chlor-4-chinolincarbonsäurechlorid    zu.

   Nach       beendigter    Reaktion     wird    die     benzolische    Lö  sung     abgetrennt,    die gebildete Base mit Salz  säure ausgezogen und mit Soda wieder ausge  fällt. Man     nimmt    die Base in Äther auf,     ver-          i.reibt    das     Lösungsmittel    und kristallisiert sie  aus     Petroläther    um.

   Das     2-,Chlor-4-chinolin-          carbonsäure,diäthyläthylendiamid    bildet farb  lose, blättrige     Kristalle    vom Schmelzpunkt       7.4'.    In den meisten organischen Lösungs  mitteln ist die     Base        leicht    löslich; mit Säu  ren bildet sie neutrale,     wasserlösliche    Salze.  



  2,5 Teile Natrium werden mit 14 Teilen       ss-Phenyl-äthylalkohol    durch     Erwärmen    in       Toluollösung    umgesetzt. Hierauf gibt man  <B>30</B> Teile     2-Chlor-4-chinolincarbonsäure-@diä-          thyläthylendiamid    hinzu     und    erwärmt im  Ölbad bis zur Beendigung der Reaktion. Man  wäscht mit Wasser aus     runddestilliert    das  Lösungsmittel im Vakuum :ab.

   Man erhält      das     2-Phenäthoxy-4-chinolincarbonsäure-di-          äthyläthylendiami-d    als<B>01,</B> das alsbald zu  farblosen Kristallen     erstarrt.    Die Base lässt  sich aus     Petroläther        umkristallisieren.     



  Zur Einführung der     Phenäthoxygruppe     können auch andere     i#letallplienylä        thylate    in  organischen     Lösungsmitteln    oder zum Bei  spiel auch Alkalien in     Gegenwart    von     (@-          Phenyläthylalko@hol    Verwendung finden.



      Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid e. It has been found that a basic derivative of a substituted quinoline carboxylic acid is obtained,

   if asymmetric diethylethylenediamine is allowed to act on acid halides of 2-halo-4-quinolinecarboxylic acid and the 2-halo-4-quinolinecarboxylic acid obtained is reacted with alkaline agents which serve to introduce the phenethoxy group.



  The 2-phenethoxy-4-quinolincarboxylic acid diethylethylenediamide forms colorless crystals with a melting point of <B> 90 '. </B> 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. Example: A solution of 1.2 parts of asymmetric diethylethylenediamine in 45 parts of 10% sodium hydroxide solution is gradually added to a benzene solution of 2.2 parts of 2-chlorine with stirring and stirring -4-quinolinecarboxylic acid chloride too.

   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 triturated and it is recrystallized from petroleum ether.

   The 2-, chloro-4-quinoline carboxylic acid, diethylethylenediamide, forms colorless, leafy crystals with a melting point of 7.4 '. The base is easily soluble in most organic solvents; with acids it forms neutral, water-soluble salts.



  2.5 parts of sodium are reacted with 14 parts of β-phenyl-ethyl alcohol by heating in toluene solution. Then 30 parts of 2-chloro-4-quinolincarboxylic acid @ diethylethylenediamide are added and the mixture is heated in an oil bath until the reaction has ended. It is washed with water and the solvent is distilled off in vacuo.

   The 2-phenethoxy-4-quinolinecarboxylic acid diethyläthylendiami-d is obtained as 01, which soon solidifies to form colorless crystals. The base can be recrystallized from petroleum ether.



  To introduce the phenethoxy group, other i # letallplienylethylates can also be used in organic solvents or, for example, alkalis in the presence of (@ - phenylethyl alcohol @ hol.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines basischen Derivates einer substituierten Chinolinearbon- säure, dadurch gekennzeichnet, dass man auf Säurehalogenide der 2-Halogen-4-chinolin- earbonsäure asymmetrisches Diäthyläthylen- diamin einwirken lässt und das erhaltene 2- Halogen -4-chinolincarbonsäure- diäthylätliy- lendiamid mit alkalischen Mitteln, ,die zur Einführung ,dar Phenäthoxygruppe dienen, PATENT CLAIM: Process for the preparation of a basic derivative of a substituted quinolinearboxylic acid, characterized in that asymmetric diethylethylene diamine is allowed to act on acid halides of 2-halogen-4-quinoline-carboxylic acid and the 2-halogen-4-quinolinecarboxylic acid diethylethyl lendiamide with alkaline agents, which serve to introduce the phenethoxy group, umsetzt. Das 2- Phenäthoxy - 4 - chinolinca.rbon- säure-diä.tliy.lithylendiamid bildet farblose Kristalle vom Schmelzpunkt<B>90'.</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- sohen Zwecken Verwendung finden. implements. The 2-phenethoxy-4-quinoline-carbonic acid-diä.tliy.lithylenediamid forms colorless crystals with a melting point <B> 90 '. </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 compound is intended to be used for therapeutic purposes.
CH139429D 1927-11-19 1927-11-19 Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. CH139429A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH139429T 1927-11-19
CH137338T 1931-12-21

Publications (1)

Publication Number Publication Date
CH139429A true CH139429A (en) 1930-04-15

Family

ID=25712939

Family Applications (1)

Application Number Title Priority Date Filing Date
CH139429D CH139429A (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) CH139429A (en)

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