CH139449A - 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
CH139449A
CH139449A CH139449DA CH139449A CH 139449 A CH139449 A CH 139449A CH 139449D A CH139449D A CH 139449DA CH 139449 A CH139449 A CH 139449A
Authority
CH
Switzerland
Prior art keywords
acid
preparation
carboxylic acid
quinolinecarboxylic acid
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 CH139449A publication Critical patent/CH139449A/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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Quinoline Compounds (AREA)

Description

  

  Verfahren zur Darstellung eines basischen Derivates einer substituierten  Chinolincar bonsäure.    Es wurde gefunden, dass man zu einem  basischen Derivat einer substituierten     Chino-          lincarbonsäure    gelangt, wenn man auf Säure  halogenide der     2-Ha1ogen-4-chinolincarbon-          säure    asymmetrisches     n-Dibutyläthylendi-          amin    einwirken lässt und das erhaltene     2-          Halogen    - 4 - chinolincarbonsäure - n -dibutyl     -          äthylendiamid    mit alkalischen Mitteln, die  zur Einführung der n-Butyloxygruppe die  nen, umsetzt.  



  Das     2-n-Butyloxy-4-chinolincarbousäure-          n-dibutyläthylendiamid    bildet farblose Kri  stalle vom Schmelzpunkt 62'. Die Base lässt  sich aus Petroläther umkristallisieren. Mit  Methansulfonsäure bildet sie ein neutrales,  wasserlösliches Salz.  



  Die neue Verbindung soll zu therapeuti  schen Zwecken Verwendung finden.  Beispiel:  Zu einer Lösung von 3,5 Teilen asym  metrischem n-Dibutyläthylendiamin in 90    Teilen 10 % iger Natronlauge gibt man unter  Kühlung und ständigem Umrühren allmäh  lich eine benzolische Lösung von 4,4 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 aus  gefällt. Man nimmt die Base in Äther auf,  vertreibt das Lösungsmittel und kristallisiert  sie aus Petroläther um. Das     2-Chlor-4-chino-          lincarbonsäure-n-dibutyläthylendiamid    bildet  farblose Kristalle vom Schmelzpunkt 59  .

    In den meisten organischen Lösungsmitteln  ist die Base leicht löslich; mit Säuren bildet  sie neutrale,wasserlösliche Salze.  Das n-Dibutyläthylendiamin (Sdp. 12  93  ) wird durch Reduktion von     n-Dibu-          tylaminoacetonitril    mit Natrium und Alko  hol erhalten.

   Das n-Dibutylaminoacetonitril       (Sdp.    12 113  )     entsteht    beider     Kondensation          von        Formarl;d@ehyd    mit     Blausäure        und        n-Di-          b.utyl:amin.         18 Teile     2-Chlor-4-chinolincarbonsäure-n-          dibutyläthylendiamid    werden mit einer Lö  sung von 1,3 Teilen Natrium in Butylalkohol  gekocht. Hierauf wird der Butylalkohol ab  destilliert, der Rückstand in Äther aufgenom  men und mit Wasser gewaschen.

   Nach Ent  fernung des Lösungsmittels verbleibt das 2       n-Butyloxy-4-chinolincarbonsäure-n-dibutyl-          äthylendiamid    als farblose Kristalle. Die  Base lässt sich aus Petroläther umkristalli  sieren.  



  Zur Einführung der n-Butyloxygruppe  können auch andere Metall-n-butylate in or  ganischen Lösungsmitteln oder zum Beispiel  auch Alkalien in Gegenwart von     n-Butyl-          alkohol    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 quinoline carboxylic acid is obtained if asymmetric n-dibutylethylenediamine is allowed to act on acid halides of 2-halo-4-quinolinecarboxylic acid and the 2-halo-4-quinolinecarboxylic acid obtained - n -dibutyl - ethylenediamide with alkaline agents, which are used to introduce the n-butyloxy group.



  The 2-n-butyloxy-4-quinolinecarbous acid n-dibutylethylenediamide forms colorless crystals with a melting point of 62 '. The base can be recrystallized from petroleum ether. With methanesulfonic acid it forms a neutral, water-soluble salt.



  The new connection is intended to be used for therapeutic purposes. Example: To a solution of 3.5 parts of asymmetric n-dibutylethylenediamine in 90 parts of 10% sodium hydroxide solution, a benzene solution of 4.4 parts of 2-chloro-4-quinolinecarboxylic acid chloride is gradually added with cooling and constant stirring. After the reaction has ended, the benzene solution is separated off, the base formed is extracted with hydrochloric acid and precipitated out again 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 n-dibutylethylenediamide forms colorless crystals with a melting point of 59.

    The base is easily soluble in most organic solvents; with acids it forms neutral, water-soluble salts. The n-dibutylethylenediamine (bp. 12 93) is obtained by reducing n-dibutylaminoacetonitrile with sodium and alcohol.

   The n-dibutylaminoacetonitrile (b.p. 12 113) results from the condensation of formarl; d @ ehyd with hydrocyanic acid and n-di-butyl amine. 18 parts of 2-chloro-4-quinolinecarboxylic acid-n-dibutylethylenediamide are boiled with a solution of 1.3 parts of sodium in butyl alcohol. The butyl alcohol is then distilled off, the residue is taken up in ether and washed with water.

   After removal of the solvent, the 2-n-butyloxy-4-quinolinecarboxylic acid-n-dibutyl-ethylenediamide remains as colorless crystals. The base can be recrystallized from petroleum ether.



  Other metal n-butylates in organic solvents or, for example, alkalis in the presence of n-butyl alcohol can also be used to introduce the n-butyloxy group.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines basischen Derivates einer substituierten Chinolincar- bonsäure, dadurch gekennzeichnet, dass man auf Säurehalogenide der 2-Halogen-4-chino- lincarbonsäure asymmetrisches n-Dibutyl- äthylendiamin einwirken lä-sst und das erhal tene 2-Halogen-4-chinolincarbonsäure-n-dibu- tyläthylendiamid mit alkalisohen Mitteln, die zur Einführung der n-Butyloxygruppe dienan, umsetzt. Das 2-n-Butyloxy-4-chinolincarbonsäure- n-dibutyläthylendiamid bildet farblose Kri stalle vom Scbmelzpunkt 62 . Claim: Process for the preparation of a basic derivative of a substituted quinolinecarboxylic acid, characterized in that asymmetric n-dibutylethylenediamine is allowed to act on acid halides of 2-halo-4-quinolinecarboxylic acid and the 2-halo-4 obtained is allowed to act Quinolincarbonsäure-n-dibutyläthylendiamid with alkalisohen agents, which dienan to introduce the n-butyloxy group, reacts. The 2-n-butyloxy-4-quinolinecarboxylic acid n-dibutylethylenediamide forms colorless crystals with a melting point of 62. Die Base lässt sich aus Petroläther umkristallisieren. Mit blethansulfonsäure bildet sie :ein neutra les, wasserlösliches .Salz. Die neue Verbindung soll zu therapen- tischen Zwecken Verwendung finden. The base can be recrystallized from petroleum ether. With methanesulfonic acid it forms: a neutral, water-soluble salt. The new connection is intended to be used for therapeutic purposes.
CH139449D 1927-11-19 1927-11-19 Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. CH139449A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH139449T 1927-11-19
CH137338T 1931-12-21

Publications (1)

Publication Number Publication Date
CH139449A true CH139449A (en) 1930-04-15

Family

ID=25712959

Family Applications (1)

Application Number Title Priority Date Filing Date
CH139449D CH139449A (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) CH139449A (en)

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