CH294889A - Method of making a durable compound of vitamin K5. - Google Patents

Method of making a durable compound of vitamin K5.

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Publication number
CH294889A
CH294889A CH294889DA CH294889A CH 294889 A CH294889 A CH 294889A CH 294889D A CH294889D A CH 294889DA CH 294889 A CH294889 A CH 294889A
Authority
CH
Switzerland
Prior art keywords
vitamin
compound
making
durable
durable compound
Prior art date
Application number
Other languages
German (de)
Inventor
Haftung Nordmark Beschraenkter
Original Assignee
Nordmark Werke 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 Nordmark Werke Gmbh filed Critical Nordmark Werke Gmbh
Publication of CH294889A publication Critical patent/CH294889A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  Verfahren zum Herstellen     einer    haltbaren Verbindung des     Vitamins    K5-    Es ist bekannt,     da.ss    das als     Vitamin        K;5     bezeichnete     1-Oxy-2-niethyl-4-a.mino-naph-          thalin-ehlorhydrat        antihämorrhagiselie    Wir  kung besitzt. Diese Verbindung ist aber an  der Luft und in wässriger Lösung     zersetzlieh     und     daher    für die medikamentöse Verabrei  chung wenig geeignet.  



  Es     wurde    nun gefunden, dass     nian    eine  Haltbare Verbindung des Vitamins     K5    herstel  len kann, wenn man in     1-Oxy-2-metliyl-4-          amino-naphthalin    die     phenolische        Hydroxyl-          riruppe    und die     Aminogruppe        acetyliert.     



       Beispiel:     <B>5</B>     o,    1-     ()        xy    - 2 -     niet        hyl-4-ainino-naplit        halin-          ehloi-hydi,at    werden in 50 g frisch destillier  tem     1'yridin    gelöst. Die Lösung färbt sich  violett. Nach einiger Zeit. ist die freie Base       breiig    ausgefallen.

   Nun werden tropfenweise       fi        g        .leetylclilorid    (auf 1     Mol    Vitamin     K5     3     11o1        Acetylehlorid)    hinzugefügt. Bei der  ersten Zugabe findet unter Erwärmen eine  heftige Reaktion statt, wobei der Brei wieder  in Lösung     #geht.    Nach     weiterer        Zugabe    des       Acet.ylcliloi-icls        srlilät    die violette Farbe in  rot um; es entsteht eine weisse kristalline  Fällung. Das     CTemiseli    bleibt 5 Stunden in    der Kälte stehen.

   Dann wird die ganze Mi  schung unter kräftigem Rühren tropfenweise  in 350     em3    10 %     iger    Schwefelsäure gegeben  und etwa 1 Stunde     st.ehengelassen.    Die Fällung  wird     abgenutscht,    mit Wasser gewaschen, die       rötliehe    Farbe mit. etwas Äther herausgelöst  und getrocknet. Die Verbindung wird in rein  weissen Kristallen in einer Ausbeute von 5,2 g  erhalten. Die Kristalle können aus 50 %     igem     Alkohol über etwas Tierkohle umkristallisiert  werden und zeigen einen     Fp.    von 194 . Der  Stickstoffgehalt, der theoretisch 5,45 % be  tragen soll, wurde mit 5,73 % gefunden.

   Die  Verbindung ist     antihämmorrhagiseh    wirksam  und im Gegensatz zum Vitamin K5 haltbar.



  Process for producing a durable compound of vitamin K5 It is known that the 1-oxy-2-niethyl-4-a.mino-naphthalene chloride hydrate, designated as vitamin K; 5, has antihemorrhagic effects. However, this compound is decomposable in the air and in aqueous solution and is therefore not very suitable for medicinal administration.



  It has now been found that a durable compound of vitamin K5 can be produced if the phenolic hydroxyl group and the amino group are acetylated in 1-oxy-2-methyl-4-amino-naphthalene.



       Example: <B> 5 </B> o, 1- () xy - 2 - niet hyl-4-ainino-naplit halin-ehloi-hydi, at are dissolved in 50 g of freshly distilled 1'yridine. The solution turns purple. After some time. the free base is pulpy.

   Now fi g .leetyl chloride (to 1 mol of vitamin K5 3 11o1 acetyl chloride) are added drop by drop. With the first addition, a vigorous reaction takes place with heating, whereby the slurry goes back into solution. After further addition of the Acet.ylcliloi-icls srlilät the violet color to red; a white crystalline precipitate is formed. The CTemiseli stays in the cold for 5 hours.

   Then the whole mixture is poured drop by drop into 350 cubic meters of 10% sulfuric acid with vigorous stirring and left to stand for about 1 hour. The precipitate is sucked off, washed with water, the reddish color with. some ether dissolved and dried. The compound is obtained in pure white crystals in a yield of 5.2 g. The crystals can be recrystallized from 50% alcohol over some animal charcoal and have a melting point of 194. The nitrogen content, which should theoretically be 5.45%, was found to be 5.73%.

   The compound is antihemorrhagic and, unlike vitamin K5, is durable.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung einer haltbaren Verbindung des Vitamins K5, dadurch gekenn zeichnet, dass man in 1-Oxy-2-methyl-4-amino- naphthalin die phenolische Hydroxylgruppe und die Aminogruppe acetyliert. Das so er haltene 1-Acetoxy-2-methyl-4-aeetylamino- naphthalin kristallisiert. aus 50 % igeln Alkohol in farblosen Kristallen von Fp. 194 . Es soll als Antihämorrhagicum verwendet werden. PATENT CLAIM: Process for the production of a durable compound of vitamin K5, characterized in that the phenolic hydroxyl group and the amino group are acetylated in 1-oxy-2-methyl-4-aminonaphthalene. The 1-acetoxy-2-methyl-4-aetylamino-naphthalene obtained in this way crystallizes. from 50% alcohol in colorless crystals of melting point 194. It is said to be used as an antihemorrhagic.
CH294889D 1944-03-16 1945-03-13 Method of making a durable compound of vitamin K5. CH294889A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE294889X 1944-03-16

Publications (1)

Publication Number Publication Date
CH294889A true CH294889A (en) 1953-11-30

Family

ID=6087653

Family Applications (1)

Application Number Title Priority Date Filing Date
CH294889D CH294889A (en) 1944-03-16 1945-03-13 Method of making a durable compound of vitamin K5.

Country Status (1)

Country Link
CH (1) CH294889A (en)

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