CH105106A - Process for the preparation of an alkoxyakridine. - Google Patents

Process for the preparation of an alkoxyakridine.

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Publication number
CH105106A
CH105106A CH105106DA CH105106A CH 105106 A CH105106 A CH 105106A CH 105106D A CH105106D A CH 105106DA CH 105106 A CH105106 A CH 105106A
Authority
CH
Switzerland
Prior art keywords
yellow
dilute
acid
ether
needles
Prior art date
Application number
Other languages
German (de)
Inventor
Leopold Cassella Co Ge Haftung
Original Assignee
Cassella Leopold & Co Gmbh
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 Cassella Leopold & Co Gmbh filed Critical Cassella Leopold & Co Gmbh
Publication of CH105106A publication Critical patent/CH105106A/en

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D219/00Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
    • C07D219/04Heterocyclic compounds containing acridine or hydrogenated acridine ring systems 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 carbon atoms of the ring system
    • C07D219/06Oxygen atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

  

  Verfahren zur Darstellung eines     Alkoxyakridins.       Es wurde gefunden, dass man     3,6-Dioxy-          akridin    (Benda, B. 45, S. 17041912) durch  Einwirkung von     Methylierungsmitteln    in den       0-Dimethyläther    überführen kann, ohne dabei  gleichzeitig den Ringstickstoff zu     alkylieren.     



  Das neue Produkt eignet sich infolge seiner       Ungiftigkeit    und starken     bakterienhemmenden     Wirkung zur Verhütung und Heilung von In  fektionen verschiedener Art. Der     Dimethyl-          äther    des     3,6-Dioxyakridins,    der sich im Tier  versuch als nahezu ungiftig erwiesen hat,  hemmt z. B. das Wachstum von     Diphterie-          bazillen    und     Streptokokken    noch in sehr grosser       Verdünnung,    während das     3,6-Dioxyakridin,     selbst in starker Konzentration, fast wirkungs  los ist.  



  Auch der     0-Monomethyläther    des     3,6-Di-          oxyakridins,    der sich neben dem     Dimethyläther     in wechselnden Mengen bildet, ist ein wert  volles     Desinfektions-    und Heilmittel.    <I>Beispiel:</I>    211     gr        3,6-Dioxy        akridin    werden in 2000 ccm  Wasser unter Zusatz von 80     gr        Ätznatron    ge  löst. Diese Lösung wird unter Rühren all-         mählich    mit 266     gr        Dimethylsulfat    versetzt.

    Man rührt, bis das     Dimethylstilfat    verschwun  den und die Lösung nahezu neutral geworden  ist, fügt dann nochmals 25     gr        Dimethylsulfat     und 16     gr        Ätznatron,    gelöst in wenig Wasser,  zu und filtriert nach Beendigung der Reaktion  das ausgeschiedene     3,6-Dimethoxyakridin    ab.  Die Rohbase wird in heisser, verdünnter Salz  säure gelöst. Aus der filtrierten Lösung kri  stallisiert das Chlorhydrat beim Abkühlen in  wenig gefärbten     Nädelchen    aus.

   Aus dem  Chlorhydrat gewinnt man in üblicher Weise  die freie Base.-  In der alkalischen Mutterlauge befindet  sich der     Monometbyläther    des     3,6-Dioxyakri-          dins.    Man gewinnt ihn aus der Lösung durch  genaues Neutralisieren mit Essigsäure.  



  Das     3,6-Dimethoxyakridin        (Ci        sHi        sNOs)     kristallisiert aus .Äther in feinen, schwach  gelblichen Nadeln oder dicken, hellgelben Kri  stallen vom Schmelzpunkt 138-139       (unkorr)     aus. Es ist leicht löslich in warmem Äther,  Alkohol, Methylalkohol, Benzol und Aceton,  wenig löslich in heissem Wasser, unlöslich in  verdünnten     Alkalien    und     Alkalikarbonaten.         Die Lösung in konzentrierter     Schwefels < i,ure     ist gelb und zeigt stark grüne Fluoreszenz.

    In Eisessig und in heissen verdünnten Mineral  säuren löst sich     Dimethoxyakridin    leicht mit  gelber Farbe und grüner Fluoreszenz; auf  Zusatz von verdünnter überschüssiger Mineral  säure kristallisieren die     betreffenden    Salze in  Form gelber Nadeln aus.



  Process for the preparation of an alkoxyakridine. It has been found that 3,6-dioxy acridine (Benda, B. 45, p. 17041912) can be converted into 0-dimethyl ether by the action of methylating agents without alkylating the ring nitrogen at the same time.



  The new product is suitable due to its non-toxicity and strong bacteria-inhibiting effect for the prevention and healing of infections of various kinds. The dimethyl ether of 3,6-Dioxyakridins, which has proven to be almost non-toxic in animal experiments, inhibits z. B. the growth of diphtheria bacilli and streptococci is still very much diluted, while 3,6-dioxyakridine, even in high concentrations, is almost ineffective.



  The 0-monomethyl ether of 3,6-dioxyacridine, which is formed in varying amounts in addition to the dimethyl ether, is also a valuable disinfectant and remedy. <I> Example: </I> 211 grams of 3,6-dioxy acridine are dissolved in 2000 ccm of water with the addition of 80 grams of caustic soda. This solution is gradually mixed with 266 grams of dimethyl sulfate while stirring.

    The mixture is stirred until the dimethyl stilfate has disappeared and the solution has become almost neutral, then another 25 grams of dimethyl sulfate and 16 grams of caustic soda, dissolved in a little water, are added and the 3,6-dimethoxyacridine which has separated out is filtered off after the reaction has ended. The raw base is dissolved in hot, dilute hydrochloric acid. From the filtered solution, the hydrated chloride crystallizes out in little colored needles on cooling.

   The free base is obtained from the chlorohydrate in the usual way. The monomethyl ether of 3,6-dioxyakridine is in the alkaline mother liquor. It is recovered from the solution by precisely neutralizing it with acetic acid.



  The 3,6-dimethoxyakridine (Ci sHi sNOs) crystallizes out. Ether in fine, pale yellowish needles or thick, light yellow crystals with a melting point of 138-139 (uncorr). It is easily soluble in warm ether, alcohol, methyl alcohol, benzene and acetone, slightly soluble in hot water, insoluble in dilute alkalis and alkali carbonates. The solution in concentrated sulfuric acid is yellow and shows strong green fluorescence.

    In glacial acetic acid and in hot diluted mineral acids, dimethoxyacridine dissolves easily with a yellow color and green fluorescence; Upon addition of dilute excess mineral acid, the salts concerned crystallize out in the form of yellow needles.

 

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung von 3,6-Dirne- thoxyakridin, darin bestehend, dass man 3,6- Dioxyakridin in Gegenwart säurebindender Mittel mit einem Methylierungsmittel behan delt. Das 3,6-Diinethoxyakridin kristallisiert aus Äther in feinen, schwach gelblichen Nadeln oderdicken, hellgelben Kristallen vom Schrnelz- punkt 138-1291 (unkorr) aus. PATENT CLAIM: Process for the preparation of 3,6-dirne thoxyakridine, which consists in treating 3,6-dioxyakridine with a methylating agent in the presence of acid-binding agents. 3,6-Diinethoxyakridine crystallizes from ether in fine, pale yellowish needles or thick, light yellow crystals with a melting point 138-1291 (uncorr). Es ist leicht löslich in warmem Äther, Alkohol, Methyl alkohol, Benzol und Aceton, wenig löslich in heissem Wasser, unlöslich in verdünnten Al- halien und Alkalikarbonaten. Die Lösung in konzentrierter Schwefelsäure ist gelb und zeigt stark grüne Fluot-eszer)z. In Eisessig und in heissen verdünnten Mineralsäuren löst sich Dimethoxyakridin leicht mit gelber Farbe und grüner Fluoreszenz; It is easily soluble in warm ether, alcohol, methyl alcohol, benzene and acetone, slightly soluble in hot water, insoluble in dilute alloys and alkali carbonates. The solution in concentrated sulfuric acid is yellow and shows strong green Fluot-eszer) z. In glacial acetic acid and in hot, dilute mineral acids, dimethoxyakridine dissolves easily with a yellow color and green fluorescence; auf Zusatz von verdünn ter überschüssiger Mineralsäure kristallisieren die betreffenden Salze in Form gelber Nadeln an". upon addition of dilute excess mineral acid, the salts concerned crystallize in the form of yellow needles ".
CH105106D 1923-04-14 1923-04-14 Process for the preparation of an alkoxyakridine. CH105106A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH105106T 1923-04-14

Publications (1)

Publication Number Publication Date
CH105106A true CH105106A (en) 1924-06-02

Family

ID=4363986

Family Applications (1)

Application Number Title Priority Date Filing Date
CH105106D CH105106A (en) 1923-04-14 1923-04-14 Process for the preparation of an alkoxyakridine.

Country Status (1)

Country Link
CH (1) CH105106A (en)

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