CH126722A - Process for the preparation of 6-ethoxy-8-aminoquinoline. - Google Patents

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

Info

Publication number
CH126722A
CH126722A CH126722DA CH126722A CH 126722 A CH126722 A CH 126722A CH 126722D A CH126722D A CH 126722DA CH 126722 A CH126722 A CH 126722A
Authority
CH
Switzerland
Prior art keywords
aminoquinoline
ethoxy
chlorohydrate
preparation
properties
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 CH126722A publication Critical patent/CH126722A/en

Links

Description

  

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

      Es wurde nun gefunden, dass das bisher  noch unbekannte     6-Äthoxy-8-aminocliinolin     ausser den schon erwähnten     antipyretischen     Eigenschaften des     5-Amine-8-äthoxychinolins     auch noch eine starke spezifisch abtötende       Wirkung    auf Blutparasiten ausübt.  



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



  Das     6-Äthoxy-8-aminochinolin    soll so  wohl selbst als Heilmittel, sowie auch als  Zwischenprodukt zur Herstellung pharma  zeutisch wertvoller Derivate Verwendung  finden.         Beispiel:     
EMI0001.0019     
    160     Gewichtsteile        6-Oxy-8-aminochinolin     werden in 400 Gewichtsteilen 10     %iger    Na  tronlauge unter Rühren gelöst und in die  klare Lösung 154 Gewichtsteile     Diäthyl-          sulfat    eingetragen. Die Flüssigkeit erwärmt  sich.     Nach    Beendigung der Reaktion werden  nochmals 400 Gewichtsteile 10     %iger    Natron  lauge zugefügt und kurz aufgekocht.

   Die  <B>L</B> 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     6-Äthoxy-8-aminochinolin    de  stilliert bei einem Druck von zirka 1 mm  bei 144 bis 145  . Das gelbe ölige Destillat  erstarrt rasch zu einer derben Kristallmasse      vom     Schmelzpunkt        -f-    60  .

   Das Chlorhydrat  dieser     Verbindung        zeigt    sehr ähnliche Eigen  schaften in bezug auf Farbe und Löslichkeit,  wie .das Chlorhydrat des     6-Methoxy-8-amino-          chinolins.  



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

      It has now been found that the hitherto unknown 6-ethoxy-8-aminocliinoline, in addition to the aforementioned antipyretic properties of 5-amine-8-ethoxyquinoline, also has a strong specific killing effect on blood parasites.



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



  The 6-ethoxy-8-aminoquinoline is supposed to be used as a remedy itself, as well as as an intermediate for the production of pharmaceutically valuable derivatives. Example:
EMI0001.0019
    160 parts by weight of 6-oxy-8-aminoquinoline are dissolved in 400 parts by weight of 10% strength sodium hydroxide solution with stirring and 154 parts by weight of diethyl 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 <B> L </B> alkaline reaction mass is extracted with ether, the ethereal solution is extracted again with sodium hydroxide solution and then with water. After drying, the ether becomes ash with pot. evaporated and the residue fractionated. The 6-ethoxy-8-aminoquinoline de stills at a pressure of about 1 mm at 144 to 145. The yellow oily distillate quickly solidifies into a coarse crystal mass with a melting point of -f- 60.

   The chlorohydrate of this compound shows properties in terms of color and solubility that are very similar to those of the chlorohydrate of 6-methoxy-8-aminoquinoline.

 

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von 6-Äthoxy- 8-aminochinolin, dadurch gekennzeichnet, dass man 6-Oxy-8-aminochinolin äthyliert. Das 6-Äthoxy-8-ami.nochinolindestilliert bei einem Druck von zirka 1 mm bei 144 bis 145 . PATENT CLAIM: Process for the production of 6-ethoxy-8-aminoquinoline, characterized in that 6-oxy-8-aminoquinoline is ethylated. The 6-ethoxy-8-ami.nochinol distills at a pressure of about 1 mm at 144 to 145. Das gelbe ölige Destillat erstarrt rasch zu einer. derben Kristallmasse vom Schmelz- Punkt + <B>60'.</B> Das Chlorhydrat dieser Ver bindung zeigt sehr ähnliche Eigenschaften in bezug auf Farbe und Löslichkeit wie das Chlorhydrat des 6-Methoxy-8-aminochinolins. Das 6-Äthoxy-8-aminochinolin soll als Heil mittel, sowie als Zwischenprodukt zur Her stellung pharmazeutisch wertvoller Derivate Verwendung finden. Neben antipyretischen Eigenschaften hat es noch eine starke spe zifisch abtötsnde Wirkung auf Blutparaeiten. The yellow oily distillate quickly solidifies into a. coarse crystal mass with a melting point of + <B> 60 '. </B> The chlorohydrate of this compound shows very similar properties in terms of color and solubility as the chlorohydrate of 6-methoxy-8-aminoquinoline. The 6-ethoxy-8-aminoquinoline is said to be used as a healing agent and as an intermediate for the manufacture of pharmaceutically valuable derivatives. In addition to antipyretic properties, it also has a strong specific killing effect on blood pairs.
CH126722D 1925-04-29 1926-04-13 Process for the preparation of 6-ethoxy-8-aminoquinoline. CH126722A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE126722X 1925-04-29
CH125476T 1926-04-13

Publications (1)

Publication Number Publication Date
CH126722A true CH126722A (en) 1928-07-02

Family

ID=25710476

Family Applications (1)

Application Number Title Priority Date Filing Date
CH126722D CH126722A (en) 1925-04-29 1926-04-13 Process for the preparation of 6-ethoxy-8-aminoquinoline.

Country Status (1)

Country Link
CH (1) CH126722A (en)

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