CH213817A - Process for the preparation of 7-iodo-5-chloro-8-oxyquinoline. - Google Patents

Process for the preparation of 7-iodo-5-chloro-8-oxyquinoline.

Info

Publication number
CH213817A
CH213817A CH213817DA CH213817A CH 213817 A CH213817 A CH 213817A CH 213817D A CH213817D A CH 213817DA CH 213817 A CH213817 A CH 213817A
Authority
CH
Switzerland
Prior art keywords
parts
oxyquinoline
chloro
iodo
iodine
Prior art date
Application number
Other languages
German (de)
Inventor
J D Riedel- Aktiengesellschaft
Original Assignee
J D Riedel E De Haeen Aktienge
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 J D Riedel E De Haeen Aktienge filed Critical J D Riedel E De Haeen Aktienge
Publication of CH213817A publication Critical patent/CH213817A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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 ring carbon atoms
    • C07D215/20—Oxygen atoms
    • C07D215/24—Oxygen atoms attached in position 8
    • C07D215/26—Alcohols; Ethers thereof
    • C07D215/28—Alcohols; Ethers thereof with halogen atoms or nitro radicals in positions 5, 6 or 7

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

Description

  

  Verfahren zur Herstellung von     7-Jod-5-chlor-8-oxychinolin.       Es ist bekannt, dass man     7-Jod-5-ehlor-8-          oxycbinolin    erhält, wenn man     5-Chlor-8-oxy-          chinolin    mit jodierenden Mitteln behandelt.  Dieses Verfahren ist aber umständlich und  liefert unbefriedigende Ausbeuten, weil man  von dem nicht leicht zugänglichen     5-Chlor-          8-oxychinolin    ausgehen muss.  



  Es wurde gefunden, dass man unter Um  gehung des     5-Chlor-8-oxychinolins    einfacher  und mit besserer Ausbeute     7-Jod-5-chlor-8-          oxychinolin    erhält, wenn man auf 8 -     Oxy-          chinolin        Jodtrichlorid    einwirken lässt.  



  Die Umsetzung kann sowohl in organi  schen     indifferen        Lösungsmitteln    oder     Lösungs-          mittelgemischen,    z. B. Chloroform,     Tetrachlor-          kohlenstoff,    Eisessig, wie auch in anorgani  schen, zum Beispiel wässerige konzentrierte       Salzsäure,    vorgenommen werden, wobei man  das     Jodtrichlorid    zweckmässig erst im Lö  sungsmittel durch     Einwirkung    von Chlor auf  elementares Jod herstellt.

      <I>Beispiel 1:</I>       In    12,7 Teile Jod, die in 80 Teilen Tetra  chlorkohlenstoff gelöst sind, wird Chlor bis       zur    Gewichtszunahme von 10,7 Teilen einge  leitet. Die dabei entstehende Lösung von       Jodtrichlorid    wird dann unter Kühlung mit  einer Lösung von 14,5 Teilen     8-Oxychiriolin     in 80 Teilen     Tetrachlorkoblenstoff    vermischt  und mehrere Stunden bei Raumtemperatur  sich selbst überlassen.

   Dabei fällt das Chlor  hydrat des     7-Jod-5-chlor-8-oxychinolins    aus,  das abgesaugt und durch     Behandlung    mit  800 Teilen Wasser in die freie Base überge  führt     wird.    Nach dem Auswaschen mit Wasser       und        Trocknen        erhält        man        29        Teile        (92        %     der theoretisch zu erwartenden Menge)     7-Jod-          5-chlor-5-oxychinolin    vom     Schmp.    178 0.

      <I>Beispiel 2:</I>  In 12,7 Teile Jod in 100 Teilen Eisessig  werden 10,7 Teile Chlor eingeleitet; die ent  standene Lösung wird unter Kühlung zu      14,5 Teilen     8-Oxychinoliri    gegeben. Nach  mehrstündigem Stehen bei Zimmertemperatur       wird    das ausgefallene Chlorhydrat wie in  Beispiel 1 aufgearbeitet und liefert 29 Teile       (95        %        der        Theorie)        7-Jod-5-elilor-8-oxycliinoliri     vom     Schmp.   <B>1790.</B>  



       Beispiel   <I>3:</I>  12,7 Teile Jod werden mit 50 Teilen       33        %iger        Salzsäure        übergossen.        Beim        Ein-          leiten    von 10,7 Teilen Chlor     entsteht    eine  rotgelbe, klare Lösung, die mit einer Lösung  von 14,

  5 Teilen     8-Oxychinolin    in 100 Teilen       33        %iger        Salzsäure        vereinigt        wird.        Das        aus-          gefallene    Chlorhydrat wird, wie im     Beispiel    1  beschrieben ist, aufgearbeitet, wobei man    29 Teile, d. h. in einer Ausbeute von 95      /o     der Theorie, reines     7-Jod-5-chlor-8-oxychiiiolin          (Schmp.    178 0) erhält.  



  In allen Fällen eignet sich das Endprodukt  als Wundantiseptikum.



  Process for the preparation of 7-iodo-5-chloro-8-oxyquinoline. It is known that 7-iodo-5-chloro-8-oxycbinoline is obtained when 5-chloro-8-oxyquinoline is treated with iodine agents. However, this process is laborious and gives unsatisfactory yields because one has to start from the not easily accessible 5-chloro-8-oxyquinoline.



  It has been found that by bypassing 5-chloro-8-oxyquinoline, 7-iodine-5-chloro-8-oxyquinoline is obtained more easily and with better yield if 8-oxyquinoline is allowed to act on iodine trichloride.



  The implementation can be carried out both in organic rule indifferent solvents or solvent mixtures, eg. B. chloroform, carbon tetrachloride, glacial acetic acid, as well as in inorganic rule, for example aqueous concentrated hydrochloric acid, can be made, the iodine trichloride is best prepared in the solvent by the action of chlorine on elemental iodine.

      <I> Example 1: </I> In 12.7 parts of iodine, which are dissolved in 80 parts of carbon tetrachloride, chlorine is introduced up to a weight increase of 10.7 parts. The resulting solution of iodine trichloride is then mixed, with cooling, with a solution of 14.5 parts of 8-oxychirioline in 80 parts of carbon tetrachloride and left to stand for several hours at room temperature.

   The chlorine hydrate of 7-iodo-5-chloro-8-oxyquinoline precipitates and is filtered off with suction and converted into the free base by treatment with 800 parts of water. After washing with water and drying, 29 parts (92% of the theoretically expected amount) of 7-iodo-5-chloro-5-oxyquinoline with a melting point of 178 ° are obtained.

      <I> Example 2 </I> 10.7 parts of chlorine are passed into 12.7 parts of iodine in 100 parts of glacial acetic acid; the resulting solution is added to 14.5 parts of 8-oxyquinolyres with cooling. After standing for several hours at room temperature, the precipitated chlorohydrate is worked up as in Example 1 and yields 29 parts (95% of theory) of 7-iodo-5-elilor-8-oxycliinoliri of melting point 1790. </B>



       Example <I> 3: </I> 50 parts of 33% hydrochloric acid are poured over 12.7 parts of iodine. When 10.7 parts of chlorine are introduced, a red-yellow, clear solution is formed which is mixed with a solution of 14,

  5 parts of 8-oxyquinoline are combined in 100 parts of 33% hydrochloric acid. The precipitated chlorohydrate is, as described in Example 1, worked up, 29 parts, i.e. H. pure 7-iodo-5-chloro-8-oxychiiioline (melting point 178 °) is obtained in a yield of 95% of theory.



  In all cases, the end product is suitable as a wound antiseptic.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von als Wund antiseptikum geeignetem 7-Jod-5-chlor-8-oxy- chinolin, dadurch gekennzeichnet, daLi inan 8-Oxychinolin mit Lösungen von Jodtrichlorid behandelt. PATENT CLAIM: Process for the production of 7-iodo-5-chloro-8-oxyquinoline suitable as a wound antiseptic, characterized in that 8-oxyquinoline is treated with solutions of iodine trichloride.
CH213817D 1938-12-07 1939-11-27 Process for the preparation of 7-iodo-5-chloro-8-oxyquinoline. CH213817A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE213817X 1938-12-07

Publications (1)

Publication Number Publication Date
CH213817A true CH213817A (en) 1941-03-15

Family

ID=5815311

Family Applications (1)

Application Number Title Priority Date Filing Date
CH213817D CH213817A (en) 1938-12-07 1939-11-27 Process for the preparation of 7-iodo-5-chloro-8-oxyquinoline.

Country Status (1)

Country Link
CH (1) CH213817A (en)

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