CH125626A - Process for the preparation of 6-isopropyloxy-8-aminoquinoline. - Google Patents

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

Info

Publication number
CH125626A
CH125626A CH125626DA CH125626A CH 125626 A CH125626 A CH 125626A CH 125626D A CH125626D A CH 125626DA CH 125626 A CH125626 A CH 125626A
Authority
CH
Switzerland
Prior art keywords
isopropyloxy
aminoquinoline
production
hydrochloric acid
preparation
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 CH125626A publication Critical patent/CH125626A/en

Links

Description

  

  Verfahren zur Darstellung von     6-Isopropyloxy-8-aminochinolin.            Amino-Derivate    von     Alkoxy-Chinolinen     sind bekannt, zum Beispiel das     5-Amino-8-          äthoxychinolin    (D. R. P. 60808, 65102,  65111), dessen     N-Acetylverbindung    bemer  kenswerte     antipyretische    Eigenschaften auf  weist.  



  Es wurde nun gefunden, dass das bisher  noch unbekannte     6-Isopropyloxy-8-amino-          chinolin    ausser den schon erwähnten     anti-          pyretischen    Eigenschaften des     5-Amino-8-          äthoxychinolins    auch noch eine starke spezi  fisch abtötende     Wirkung    auf Blutparasiten  ausübt.  



  Gemäss dem Verfahren der vorliegenden  Erfindung wird diese Verbindung erhalten  durch Reduktion eines     6-Isopropyloxychino-          lins,    welches in     8-Stellung    einen zur     Amino-          CY          ruppe    reduzierbaren stickstoffhaltigen     Sub-          stituenten    aufweist. zum Beispiel durch Re  duktion von     6-Isoprö-pyloxy-8-nitrochinolin     oder von     6-Isopropyloxy-8-azoarylchinolin.     



  Das     6-Isopropyloxy-8-aminochinolin    soll  sowohl selbst als Heilmittel, sowie auch als  Zwischenprodukt zur Herstellung pharma-         zeutisch    wertvoller Derivate Verwendung  finden.  



       Beispiel:     
EMI0001.0028     
    5,0 kg     6-Isopropyloxy-8-nitrochinolin     werden in 20 Litern reiner konzentrierter  Salzsäure gelöst und warm eingegossen in 60  Liter einer     Zinnchlorürlösung,    die 600     gr          Zinnchlorür    in     I.    Liter Lösung enthält. Nach  einstündigem Erhitzen auf     -f-    100   werden  100 Liter konzentrierter Salzsäure zuge  geben, das nach .dem Erkalten abgeschiedene       Chlorzinndoppelsalz    abgesaugt, mit Salz  säure gewaschen und in üblicher Weise zer  legt.  



  Das so erhaltene     6-Isopropy        loxy-8-amino-          chinolin    siedet unter einem Druck von 2 mm  bei 149 bis 150  . Es stellt eine hellgelbe,  dicke Flüssigkeit dar und bildet mit Salz-      säure ein im Wasser ziemlich schwer lös  liches,     gelbes,    kristallines     Chlorhydrad.  



  Process for the preparation of 6-isopropyloxy-8-aminoquinoline. Amino derivatives of alkoxy quinolines are known, for example 5-amino-8-ethoxyquinoline (D. R. P. 60808, 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 aforementioned antipyretic properties of 5-amino-8-ethoxyquinoline, also has a strong specific killing effect on blood parasites.



  According to the process of the present invention, this compound is obtained by reducing a 6-isopropyloxyquinoline which has a nitrogen-containing substituent which can be reducible to the amino-CY group in the 8-position. for example by reducing 6-isopropyloxy-8-nitroquinoline or 6-isopropyloxy-8-azoarylquinoline.



  The 6-isopropyloxy-8-aminoquinoline is said to be used both as a medicinal product itself and as an intermediate for the production of pharmaceutically valuable derivatives.



       Example:
EMI0001.0028
    5.0 kg of 6-isopropyloxy-8-nitroquinoline are dissolved in 20 liters of pure concentrated hydrochloric acid and poured warm into 60 liters of a tin chloride solution containing 600 g of tin chloride in 1 liter of solution. After heating to -f- 100 for one hour, 100 liters of concentrated hydrochloric acid are added, and the chlorotin double salt which separates out after cooling is suctioned off, washed with hydrochloric acid and decomposed in the usual way.



  The 6-isopropyloxy-8-aminoquinoline obtained in this way boils at 149 to 150 under a pressure of 2 mm. It is a light yellow, thick liquid and, together with hydrochloric acid, forms a yellow, crystalline hydrochloride that is rather poorly soluble in water.

 

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von 6-Isopro- pyloxy-8-aminochinolin, dadurch gekenn zeichnet, dass man ein 6-Isopropyloxychino- lin, welches in 8-Stellung einen zur Amino- gruppe reduzierbaren stickstoffhaltigen Sub- stituenten aufweist, reduziert. Das 6-Isopro- pyloxy-8-aminochinolin siedet unter einem Druck von Z mm bei 149 bis<B>150</B> . PATENT CLAIM: Process for the production of 6-isopropyloxy-8-aminoquinoline, characterized in that a 6-isopropyloxyquinoline, which has a nitrogen-containing substituent which can be reducible to the amino group in the 8-position, is reduced. The 6-isopropyloxy-8-aminoquinoline boils under a pressure of Z mm at 149 to 150. Es stellt eine hellgelbe diele Flüssigkeit dar und bil- det mit Salzsäure ein im Wasser ziemlich schwer lösliches, gelbes, kristallines Chlor hydrat. Das 6-lsohropyloxy-8-aminochino-lin soll als Heilmittel, sowie als Zwischenprodukt zur Herstellung pharmazeutisch wertvoller De rivate Verwendung finden. Neben antipyre- tischen Eigenschaften hat es noch eine starke spezifisch abtötende 'N#@'irkung auf Blutpara siten. It is a light yellow liquid and, together with hydrochloric acid, forms a yellow, crystalline chlorohydrate that is rather poorly soluble in water. The 6-isohropyloxy-8-aminochino-lin 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.
CH125626D 1925-04-29 1926-04-13 Process for the preparation of 6-isopropyloxy-8-aminoquinoline. CH125626A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE125626X 1925-04-29
CH121343T 1926-04-13

Publications (1)

Publication Number Publication Date
CH125626A true CH125626A (en) 1928-04-16

Family

ID=25709667

Family Applications (1)

Application Number Title Priority Date Filing Date
CH125626D CH125626A (en) 1925-04-29 1926-04-13 Process for the preparation of 6-isopropyloxy-8-aminoquinoline.

Country Status (1)

Country Link
CH (1) CH125626A (en)

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