CH139435A - 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
CH139435A
CH139435A CH139435DA CH139435A CH 139435 A CH139435 A CH 139435A CH 139435D A CH139435D A CH 139435DA CH 139435 A CH139435 A CH 139435A
Authority
CH
Switzerland
Prior art keywords
preparation
acid
basic derivative
carboxylic acid
petroleum ether
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 CH139435A publication Critical patent/CH139435A/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)

Description

  

  Verfahren zur Darstellung eines     basischen    Derivates einer substituierten       Chinolinea.rbonsäur    e.    Es wurde gefunden,     da:ss    man zu :einem  basischen     Deiivat    einer     substituierten        Ghino-          lincarhonsäure    gelangt, wenn man auf     Säure-          halogenide    der     2-,H,

  al.ogen-4-eb@nolincar!bon-          säure        Triäthyläthylendiamin        einwirken    lässt  und .das erhaltene     r2-Halogen-4-chinolinear-          bonsäure-triäthylä-thylendiamid    mit     Mitteln,     die zur     Einführung    der     n-Butyloxygruppe     dienen,     umsetzt.     



  Das     2-n-Butyl:oxy-4-chinolinearbonsäure-          triäthyläthylendiamid    bildet farblose Kri  stalle vom     Schmelzpunkt    65   und vom Siede  punkt<B>163'</B> bei 0,01 mm Druck. 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 therapeu  tischen Zwecken Verwendung finden.  <I>Beispiel</I>  Zu einer     Lösung    von 1,5 \feilen     Triäthyl-          äthylendiamin    (farblose Base vom Siedepunkt         11;

  0-165     , dargestellt durch Reduktion des       Kondensationsproduktes    aus     as.        Diäthyläthy-          lendiamin        und        Acetalde.hyd    vom Siedepunkt  40'     bei    7 mm     Druck)    in 4 Teilen 10 %     iger     Natronlauge lässt man unter Rühren und  Kühlen eine     benzolisehe    Lösung von 2,2 Tei  len     2-C.hlor-4-chin:olincarbonsäurechlorid    all  mählich zufliessen.

   Nach beendeter Reaktion  wird mit Wasser gewaschen und das Lö  sungsmittel     abJestilliert.    Das     2-Chlor-4-ehi-          nolincar'bonsäure-triä(thyläthylendiamid    bil  det ein gelbliches 01 vom Siedepunkt<B>165'</B>  bei     etwa    0,015 mm Druck. In organischen  Lösungsmitteln ist es leicht löslich. Mit  Säuren gibt die Base neutrale, wasserlösliche  Salze.  



  33 Teile     2-C:hlor-4-chinolincarbonsäizre-          triäthyläthylen:diami.d    werden mit einer     IA-          sung    von 2,6 Teilen     Natrium    in     n-Butyl-          ;@lkohol        ge=kocht.    Hierauf wird der n-     Butyl-          alkohol        abdestilliert,    der Rückstand in Äther  aufgenommen und mit Wasser gewaschen.

    Nach Entfernung des Lösungsmittels ver-      bleibt     d.as        2-n-Butyloxy-4-chinolincarbon-          säure-triäthyläthylendiamid    als hellgelbes  01, das allmählich erstarrt. Die Base lässt  sich im Vakuum destillieren und aus     Petrol-          äther        umkristallisieren.     



  Zur     Einführung-    der     n-Butyloxygruppe          können    auch andere     Metall-n-buty        late    in or  ganischen Lösungsmitteln oder zum Beispiel  Alkalien in Gegenwart von     n-Butylalkohol     Verwendung finden.



  Process for the preparation of a basic derivative of a substituted quinolinea.rbonsäur e. It has been found that: a basic derivative of a substituted ghinolincarboxylic acid is obtained if one uses acid halides of the 2-, H,

  al.ogen-4-eb@nolincar!bon- säure triethylethylenediamine can act and .the resulting r2-halogen-4-quinolinear- triethylethylenediamide with agents that serve to introduce the n-butyloxy group, converts.



  The 2-n-butyl: oxy-4-quinolinearboxylic acid triethylethylenediamide forms colorless crystals with a melting point of 65 and a boiling point of <B> 163 '</B> at 0.01 mm pressure. 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. <I> Example </I> To a solution of 1.5 \ files triethylethylenediamine (colorless base with boiling point 11;

  0-165, prepared by reducing the condensation product of as. Diethyläthylenediamine and Acetalde.hyd of boiling point 40 'at 7 mm pressure) in 4 parts of 10% sodium hydroxide solution, a benzene solution of 2.2 parts is allowed with stirring and cooling 2-C.hlor-4-quin: olincarboxylic acid chloride gradually flow in.

   When the reaction has ended, it is washed with water and the solvent is distilled off. The 2-chloro-4-ehinolincarboxylic acid triethylenediamide forms a yellowish oil with a boiling point of <B> 165 '</B> at about 0.015 mm pressure. It is easily soluble in organic solvents. With acids there are Base neutral, water-soluble salts.



  33 parts of 2-C: chloro-4-quinolincarboxylic acid triethylethylene: diami.d are boiled with a solution of 2.6 parts of sodium in n-butyl alcohol. The n-butyl alcohol is then distilled off, the residue is taken up in ether and washed with water.

    After removing the solvent, the 2-n-butyloxy-4-quinolinecarboxylic acid triethylethylenediamide remains as a light yellow oil that gradually solidifies. The base can be distilled in vacuo and recrystallized from petroleum ether.



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

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines basischen Derivates einer substituierten 'Chinolimcar- bonsäure, dadurch gekennzeichnet, (ass man auf ,Säurehalogenide der 2=HalogBn-4-chino- lincarbonsäure Triäthyläthylendiamin -ein- wirken lässt und das erhaltene 2:Halogen- 4-chinolincarbonsäure-triäthyläthylendiamid mit Mitteln, .die zur Einführung der n-Butyl- oxygruppedienen, umsetzt. PATENT CLAIM: A process for the preparation of a basic derivative of a substituted quinolimecarboxylic acid, characterized in that, acid halides of the 2 = halo-4-quinolinecarboxylic acid triethylethylenediamine are allowed to act and the 2: halo-4-quinolinecarboxylic acid obtained -triäthyläthylendiamid with agents, .die for the introduction of the n-butyl oxygroup is implemented. Das 2-n-Butyloxy-4-chinolincarbons#Lure- triäthylätIlylen.diamid bildet farblose Kri stalle vom ,Schmelzpunkt G5 und vom Siede punkt<B>163</B> bei<B>0,01</B> mm Druck. 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 therapeu tischen Zwecken Verwendung finden. . The 2-n-butyloxy-4-quinolinecarbons # LuretriäthylätIlylen.diamid forms colorless crystals with melting point G5 and boiling point <B> 163 </B> at <B> 0.01 </B> mm pressure. 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. .
CH139435D 1927-11-19 1927-11-19 Process for the preparation of a basic derivative of a substituted quinoline carboxylic acid. CH139435A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH139435T 1927-11-19
CH137338T 1931-12-21

Publications (1)

Publication Number Publication Date
CH139435A true CH139435A (en) 1930-04-15

Family

ID=25712945

Family Applications (1)

Application Number Title Priority Date Filing Date
CH139435D CH139435A (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) CH139435A (en)

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