CH296572A

CH296572A - Process for the preparation of a new phenanthroline quinone.

Info

Publication number: CH296572A
Authority: CH
Inventors: Aktiengesellschaft Ciba
Original assignee: Ciba Geigy
Priority date: 1950-05-05
Filing date: 1950-05-05
Publication date: 1954-02-15

Description

  

  Verfahren     zur    Herstellung eines neuen     Phenanthrolinehinons.       Gegenstand des vorliegenden Patentes ist  ein Verfahren zur Herstellung eines neuen       Phenanthrolinehinons,    welches dadurch ge  kennzeichnet ist, dass man eine Verbindung  der Formel  
EMI0001.0004     
    worin einer der beiden Reste X und V Was  serstoff und der andere einen durch Oxyda  tion in die     Oxogruppe        überführbaren        Substi-          inent.en,

      wie eine freie oder     verätherte        Oxy-          gruppe    oder eine freie oder     aeylierte        Amino-          riruppe,    darstellt, mit. Salpetersäure oxydiert.  



  Das so erhaltene     3-3leth@-1-4,7-phenanthi@o-          lin-5,6-ehinon    der Formel  
EMI0001.0017     
         @elmiilzt    bei 230  (unter Zersetzung). Es be  sitzt     amoebicicle        Wirkung    und soll als Heilmit  tel oder als Zwischenprodukt zur Herstellung  von Heilmitteln verwendet werden.  



  Die Oxydation mit Salpetersäure wird     vor-          zugsweise    in Gegenwart von Schwefelsäure  bei erhöhter Temperatur, z. B. 50 bis 150 ,       durchgeführt.     



       Beispiel:     ?0 Gewichtsteile     3-llethyl-6-metlioxy-4,7-          phenanthrolin    werden mit<B>100</B>     Volumteilen            konz.    Schwefelsäure und unter guter Küh  lung mit 60     Volumteilen    rauchender Salpeter  säure (d = 1,51) versetzt. Man erhitzt wäh  rend 3 Stunden auf 120 , bringt dann die  Reaktionslösung auf Eis, stellt mit     10n-Na-          tronlauge    auf PH = 6-7 und putscht von dem  ausgefallenen gelben Niederschlag ab.

   Aus  wenig siedendem Methanol wird das     3-llethyl-          4,7-phenanthrolin-5,6-chinon    der Formel  
EMI0001.0034     
    in weissen Kristallen erhalten, die im Vakuum  bei 100  unter Gelbfärbung und     lIethanol-          abgabe    verwittern und einen F. = 230  unter  Zersetzung zeigen.



  Process for the production of a new phenanthrolinehinone. The present patent is a process for the preparation of a new Phenanthrolinehinons, which is characterized in that a compound of the formula
EMI0001.0004
    wherein one of the two radicals X and V is hydrogen and the other is a substituent which can be converted into the oxo group by oxidation,

      such as a free or etherified oxy group or a free or aylated amino group, with. Nitric acid oxidizes.



  The 3-3leth @ -1-4,7-phenanthi @ olin-5,6-ehinone of the formula obtained in this way
EMI0001.0017
         @elmiilzt at 230 (with decomposition). It has an amoebicicle effect and is intended to be used as a medicinal product or as an intermediate in the manufacture of medicinal products.



  The oxidation with nitric acid is preferably carried out in the presence of sulfuric acid at an elevated temperature, e.g. B. 50 to 150 carried out.



       Example: 0 parts by weight of 3-llethyl-6-metlioxy-4,7-phenanthroline are concentrated with <B> 100 </B> parts by volume. Sulfuric acid and with good cooling with 60 parts by volume of fuming nitric acid (d = 1.51). The mixture is heated to 120 for 3 hours, then the reaction solution is placed on ice, adjusted to pH = 6-7 with 10N sodium hydroxide solution and the yellow precipitate which has separated out is peeled off.

   3-llethyl-4,7-phenanthroline-5,6-quinone of the formula is obtained from low-boiling methanol
EMI0001.0034
    Obtained in white crystals, which weather in a vacuum at 100 with yellow coloration and release of ethanol and show a F. = 230 with decomposition.

Claims

<B> PATENT CLAIM: </B> Process for the preparation of a new phenanthrolinequinone, characterized in that a compound of the formula. EMI0001.0038 in which one of the two radicals X and Ir is hydrogen and the other is a substituent which can be converted into the oxo group by oxidation, oxidized with nitric acid. The 3-methyl-4,7-phenanthroline-5,6-quinone of the formula obtained in this way EMI0002.0001 melts at 230 (with decomposition).

It has an amoebicidal effect and is intended to be used as a medicinal product or as an intermediate in the manufacture of medicinal products. SUBClaims: 1. Process according to claim, characterized in that the reaction is carried out in the presence of concentrated Schrefelic acid. 2. The method according to claim and sub-claim 1, characterized in that the reaction is carried out at an elevated temperature. 3.

Process according to patent claim and dependent claims 1 and 2, characterized in that 3-methyl-6-methoxy-4,7-phenanthroline is used as the starting material.