CH126723A - Process for the preparation of 6-isopropyloxy-8-aminoquinoline. - Google Patents

Process for the preparation of 6-isopropyloxy-8-aminoquinoline.

Info

Publication number
CH126723A
CH126723A CH126723DA CH126723A CH 126723 A CH126723 A CH 126723A CH 126723D A CH126723D A CH 126723DA CH 126723 A CH126723 A CH 126723A
Authority
CH
Switzerland
Prior art keywords
aminoquinoline
isopropyloxy
preparation
production
yellow
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 CH126723A publication Critical patent/CH126723A/en

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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

  

  Verfahren zur Darstellung von     6-ISopropylogy-8-aminochinolin.            Aminoderivate    von     Alkoxychinolinen    sind  bekannt,     zum    Beispiel das.     5-Amino-8-          äthoxychinolin    (D. R. P. Nr. 60308, 65102,  65111), dessen     N-Acetylverbindung        bemer-          kenswerte        .antipyretische    Eigenschaften auf  weist.  



  Es wurde nun gefunden,     da.ss    das bisher  noch unbekannte     6-Isopropyloxy-8-aminochi-          nolin    ausser den schon erwähnten     antipyre-          ti'schen    Eigenschaften des     5-Amino-8-äthoxy-          chinolins    auch noch eine starke spezifisch ab  tötende Wirkung auf     Blutparasiten    ausübt.  



  Gemäss dem Verfahren der vorliegenden  Erfindung wird diese Verbindung hergestellt  durch     Isopropylierung    der     Hydroxylgruppe     des     6-Oxy-8-aminochinolins.     



  Das     6-Isopropyloxy-8-a.minochinolin    soll  sowohl selbst als Heilmittel, sowie auch als  Zwischenprodukt zur Herstellung pharma  zeutisch wertvoller Derivate Verwendung  finden.  
EMI0001.0023     
    160 Gewichtsteile     6-Oxy-8-aminochinolin     werden in 400     Gewichtsteilen        1,0        %iger    Na  tronlauge unter Rühren gelöst und in die  klare Lösung 182     Gewichtsteile        Diisopropyl-          sulfat    eingetragen. Die Flüssigkeit erwärmt  sich.

   Nach Beendigung der Reaktion werden  nochmals 400 Gewichtsteile 10     %iger    Natron  lauge zugefügt     und    kurz aufgekocht. Die  alkalische Reaktionsmasse wird     ausgeäthert,     die Ätherlösung mit Natronlauge und darauf       mit    Wasser     nochmals    ausgeschüttelt. Der  Äther wird nach dem Trocknen mit Pott  asche verdampft und der Rückstand frak  tioniert.  



  Das gebildete     6-Isopropyloxy-8-amino-          chinolin    siedet unter einem Druck von 2 mm  bei     149,-bis   <B>150'.</B> Es stellt eine hellgelbe           dicke    Flüssigkeit dar und bildet mit Salz  säure ein in Wasser ziemlich schwer lös  liches, gelbes, kristallines Chlorhydrat.



  Process for the preparation of 6-isopropylogy-8-aminoquinoline. Amino derivatives of alkoxyquinolines are known, for example 5-amino-8-ethoxyquinoline (D. R. P. No. 60308, 65102, 65111), the N-acetyl compound of which has remarkable antipyretic properties.



  It has now been found that the hitherto unknown 6-isopropyloxy-8-aminoquinoline, in addition to the already mentioned antipyretic properties of 5-amino-8-ethoxyquinoline, also has a strong, specific killing effect Blood parasites.



  According to the process of the present invention, this compound is prepared by isopropylating the hydroxyl group of 6-oxy-8-aminoquinoline.



  The 6-isopropyloxy-8-a.minochinolin is said to be used both as a remedy and as an intermediate for the production of pharmaceutically valuable derivatives.
EMI0001.0023
    160 parts by weight of 6-oxy-8-aminoquinoline are dissolved in 400 parts by weight of 1.0% strength sodium hydroxide solution with stirring and 182 parts by weight of diisopropyl sulfate are added to the clear solution. The liquid heats up.

   After the reaction has ended, another 400 parts by weight of 10% strength sodium hydroxide solution are added and the mixture is briefly boiled. The alkaline reaction mass is extracted with ether, the ethereal solution extracted with sodium hydroxide solution and then with water again. After drying, the ether is evaporated with pot ash and the residue is fractionated.



  The 6-isopropyloxy-8-aminoquinoline that is formed boils under a pressure of 2 mm at 149 to 150 '. It is a light yellow, thick liquid and, with hydrochloric acid, forms quite difficult in water soluble, yellow, crystalline hydrochloride.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von 6-Iso- propylo@xy-8-aminochinolin, dadurch gekenn zeichnet, dass man 6-Oxy-8-aminochinolin isopropyliert. Das 6-Isopropyloxy-8-amino- chinolin siedet unter einem Druck von 2 mm bei 149 bis<B>150'.</B> Es stellt eine hellgelbe dicke Flüssigkeit dar und bildet mit Salz- säure ein in Wasser ziemlich schwer lös liches, gelbes, kristallines Chlorhydrat. PATENT CLAIM: Process for the production of 6-isopropylo @ xy-8-aminoquinoline, characterized in that 6-oxy-8-aminoquinoline is isopropylated. The 6-isopropyloxy-8-aminoquinoline boils under a pressure of 2 mm at 149 to <B> 150 '. </B> It is a light yellow, thick liquid and, with hydrochloric acid, forms a liquid that is rather poorly soluble in water , yellow, crystalline hydrochloride. Das 6-Isopropyloxy-8-aminochinolin soll als Heilmittel, sowie als Zwischenprodukt zur Herstellung pharmazeutisch wertvoller Derivate Verwendung finden. Neben anti- pyretischen Eigenschaften hat es noch eine starke spezifisch abtötende Wirkung auf Blutparasiten. The 6-isopropyloxy-8-aminoquinoline is said to be used as a remedy and as an intermediate for the production of pharmaceutically valuable derivatives. In addition to antipyretic properties, it also has a strong, specific killing effect on blood parasites.
CH126723D 1925-04-29 1926-04-13 Process for the preparation of 6-isopropyloxy-8-aminoquinoline. CH126723A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE126723X 1925-04-29
CH125476T 1926-04-13

Publications (1)

Publication Number Publication Date
CH126723A true CH126723A (en) 1928-07-02

Family

ID=25710477

Family Applications (1)

Application Number Title Priority Date Filing Date
CH126723D CH126723A (en) 1925-04-29 1926-04-13 Process for the preparation of 6-isopropyloxy-8-aminoquinoline.

Country Status (1)

Country Link
CH (1) CH126723A (en)

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