CH212590A - Process for the preparation of a quinoline compound containing a basic substituted amino group in the 4-position. - Google Patents

Process for the preparation of a quinoline compound containing a basic substituted amino group in the 4-position.

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Publication number
CH212590A
CH212590A CH212590DA CH212590A CH 212590 A CH212590 A CH 212590A CH 212590D A CH212590D A CH 212590DA CH 212590 A CH212590 A CH 212590A
Authority
CH
Switzerland
Prior art keywords
preparation
amino group
compound containing
substituted amino
quinoline compound
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellsc Farbenindustrie
Original Assignee
Ig Farbenindustrie Ag
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 Ig Farbenindustrie Ag filed Critical Ig Farbenindustrie Ag
Publication of CH212590A publication Critical patent/CH212590A/en

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Description

  

  Verfahren zur Herstellung einer in     4.Stellung    eine basisch substituierte       Aminogruppe    enthaltenden     Chinolinverbindung.       Das     Hauptpatent    betrifft ein Verfahren  zur Herstellung einer     therapeutisch    wertvollen       Chinolinverbindung.     



  Gegenstand des vorliegenden Patentes ist  ein Verfahren zur Herstellung einer in 4  Stellung eine basisch     substituierte        Amino-          gruppe    enthaltenden     Chinolinverbindung.     Das Verfahren ist dadurch     gekennzeichnet,     dass man     3-Methyl-4-chlor-7-bromchinolin    mit       1-Diäthylamino-4-aminopentan    zum     3-Me-          thyl    -4 - (5'-     diäthylaminopentyl-        2'-        amino)    -     7-          bromchinolin    umsetzt.

   die Umsetzung erfolgt  zum Beispiel durch Erwärmen der     genannten     Ausgangsstoffe auf höhere     Temperaturen,     zum Beispiel auf     etwa    150 bis<B>160'.</B> Die  Aufarbeitung der Reaktionsmischung erfolgt  zum Beispiel in üblicher Weise. Das so er  haltene Produkt destilliert nach Entfernen  des Äthers bei     23011    unter 0,5 mm     Druck.     



  Das neue Produkt soll therapeutische An  wendung finden.    <I>Beispiel:</I>    25,6 g     3-Methyl-4-chlor-7-bromchinolin     vom Siedepunkt 150 bis 160   bei 2 mm  Druck werden mit 31,6 g     1-Diäthylamino-4-          aminopentan    und 10g Phenol 15     Stunden     in einem Ölbad von 150     bis    160   erhitzt. Die  erkaltete Schmelze wird in verdünnter Essig  säure gelöst, filtriert und     zur        Entfernung     des Phenols zweimal mit Äther gewaschen.

    Dann wird die essigsaure Lösung mit Na  tronlauge alkalisch gemacht und die abge  schiedene Base     in    Äther aufgenommen, mit  Wasser gewaschen     und    mit Pottasche ge  trocknet. Das     3-Methyl-4-(5'-diäthylamino-          pentyl-2'-amino)-7-bromchinolin    destilliert  nach     Entfernung    des Äthers bei 230       unter     0,5     mm    Druck.



  Process for the preparation of a quinoline compound containing a basic substituted amino group in the 4th position. The main patent relates to a process for the preparation of a therapeutically useful quinoline compound.



  The present patent relates to a process for the preparation of a quinoline compound containing a basic substituted amino group in position 4. The process is characterized in that 3-methyl-4-chloro-7-bromoquinoline is mixed with 1-diethylamino-4-aminopentane to give 3-methyl -4 - (5'-diethylaminopentyl-2'-amino) - 7- bromoquinoline converts.

   the reaction takes place, for example, by heating the starting materials mentioned to higher temperatures, for example to about 150 to 160 '. The reaction mixture is worked up, for example, in the customary manner. The product obtained in this way distilled after removing the ether at 23011 under 0.5 mm pressure.



  The new product is intended to find therapeutic applications. <I> Example: </I> 25.6 g of 3-methyl-4-chloro-7-bromoquinoline with a boiling point of 150 to 160 at 2 mm pressure are mixed with 31.6 g of 1-diethylamino-4-aminopentane and 10 g of phenol 15 Heated in an oil bath from 150 to 160 hours. The cooled melt is dissolved in dilute acetic acid, filtered and washed twice with ether to remove the phenol.

    Then the acetic acid solution is made alkaline with sodium hydroxide solution and the separated base is taken up in ether, washed with water and dried with potash. The 3-methyl-4- (5'-diethylaminopentyl-2'-amino) -7-bromoquinoline distilled after removal of the ether at 230 under 0.5 mm pressure.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung einer in 4 Stellung eine basisch substituierte Amino- gruppe enthaltenden Chinolinverbindung, da durch gekennzeichnet, dass man 3-Methyl- 4-chlor-7-bromchinolin mit 1-Diäthy lamino-4- aminopentan zum 3 - Methyl - 4 - (5'- diäthyl- aminopentyl-2'-a.mino)-7-bromehinolin um setzt. Das so erhaltene Produkt destilliert nach Entfernen des Äthers bei 230 unter 0,5 mm Druck. PATENT CLAIM: Process for the preparation of a quinoline compound containing a basic substituted amino group in the 4 position, characterized in that 3-methyl-4-chloro-7-bromoquinoline is used with 1-diethy lamino-4-aminopentane to give 3-methyl-4 - (5'- diethyl aminopentyl-2'-a.mino) -7-bromoehinoline is implemented. The product obtained in this way distilled after removal of the ether at 230 under 0.5 mm pressure.
CH212590D 1937-10-07 1938-09-15 Process for the preparation of a quinoline compound containing a basic substituted amino group in the 4-position. CH212590A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE212590X 1937-10-07
CH209465T 1938-09-15

Publications (1)

Publication Number Publication Date
CH212590A true CH212590A (en) 1940-11-30

Family

ID=25724726

Family Applications (1)

Application Number Title Priority Date Filing Date
CH212590D CH212590A (en) 1937-10-07 1938-09-15 Process for the preparation of a quinoline compound containing a basic substituted amino group in the 4-position.

Country Status (1)

Country Link
CH (1) CH212590A (en)

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