CH315083A - Process for the preparation of a new aldehyde derivative - Google Patents

Process for the preparation of a new aldehyde derivative

Info

Publication number
CH315083A
CH315083A CH315083DA CH315083A CH 315083 A CH315083 A CH 315083A CH 315083D A CH315083D A CH 315083DA CH 315083 A CH315083 A CH 315083A
Authority
CH
Switzerland
Prior art keywords
aldehyde derivative
pyridine
amide
dicarboxylic acid
preparation
Prior art date
Application number
Other languages
German (de)
Inventor
Hans Dr Suter
Ernst Dr Habicht
Original Assignee
Cilag 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 Cilag Ag filed Critical Cilag Ag
Publication of CH315083A publication Critical patent/CH315083A/en

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
    • C07D213/78Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81Amides; Imides
    • C07D213/82Amides; Imides in position 3
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/44Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids

Description

       

  Verfahren zur Herstellung eines neuen     Aldehydderivates       Gegenstand des Patentes ist ein Verfah  ren zur Herstellung eines neuen Aldehyd  derivates, welches gute keimtötende Eigen  schaften besitzt. Die Verbindung und haupt  sächlich auch ihre löslichen Salze sollen zur  Bekämpfung von Infektionskrankheiten ver  wendet werden.  



  Das den Gegenstand des Patentes bildende  Verfahren ist dadurch gekennzeichnet, dass  man auf     Pyridin-2,5-dicarbonsäure-5-amid     Formaldehyd einwirken, lässt, wobei sich das       Pyridin-2,5-dicarbonsättre-5-N-oxymethyl-amid     bildet. Der Formaldehyd kann beispielsweise  auch einer Formaldehyd liefernden Verbin  dung, z. B. einem polymeren Formaldehyd       (Triozymethylen,        Paraformaldehyd),    entstam  men. Vorzugsweise wird die     Umsetzung    in  alkalischem Milieu vorgenommen, da beim  Arbeiten unter     pH-7    leicht unerwünschte Ne  benprodukte entstehen.

      <I>Beispiel</I>  200 g     Pyridin-2,5-dicarbonsäure-5-amid     werden in 600     cm3    Wasser aufgeschlämmt und  unter Rühren verdünnte Natronlauge 1 :10  bis     p$    = 9 zugesetzt. Man erwärmt auf dem  Wasserbad auf 80  und verrührt mit 450     cm3          361/oiger    wässeriger     Formaldehydlösung.    Man  hält 15 Minuten bei 80  und stellt die Was  serstoffionenkonzentration mit Hilfe von Na  tronlauge auf einen Wert von 9-10 ein. Da  nach setzt man Aktivkohle zu, filtriert und    neutralisiert mit Ameisensäure genau auf       p$    7. Anschliessend rührt man Aceton ein,  bis ein Niederschlag entsteht.

   Derselbe wird  nach 24 Stunden abgesaugt und mit Aceton  gewaschen. Durch Vakuumtrocknung bei 30 bis  40  erhält man das     Natriumsalz    des     Pyridin-          2,5-dicarbonsäure-5-N-oxymethyl-amids    als  farbloses Pulver, das sich in kaltem Wasser  bis zu 20  /o mit praktisch neutraler Reaktion  löst.  



  Das so erhaltene     Natriumsalz    kann sehr  leicht aus Wasser mit Hilfe von Aceton um  gefällt werden.  



  Die freie Verbindung kann durch vor  sichtiges     Ansäuern    der wässerigen Lösung  eines Salzes des     Pyridin-2,5-dicarbonsäure-5-          N-oxymethyl-amids    erhalten werden. Sie stellt  ein farbloses Pulver dar, das keinen scharfen       Schmelzpunkt    zeigt, sondern sieh beim Erwär  men langsam zersetzt.  



  Die Salze der neuen Verbindung sind sehr  beständig. Ihre wässerigen Lösungen reagie  ren nahezu neutral und sind für Injektionen  vorzüglich geeignet.  



  Die neue Verbindung lässt sieh beispiels  weise leicht in Form ihrer Salze, z. B. des  Natriums,     Kalziums,    oder von     Aminen,    wie  von     Diäthylamin,        Diäthanolamin,        Morpholin     usw., isolieren. Zu diesem Zwecke kann man,  wie im Beispiel näher beschrieben, das dem       verwendeten    alkalischen Kondensationsmittel      entsprechende Salz durch Vermischen der  Reaktionslösung mit einer organischen, mit       Vrasser    mischbaren Lösungsmittel ausfällen.



  Process for the preparation of a new aldehyde derivative The subject of the patent is a process for the preparation of a new aldehyde derivative which has good germicidal properties. The compound and mainly its soluble salts are intended to be used to combat infectious diseases.



  The method forming the subject of the patent is characterized in that pyridine-2,5-dicarboxylic acid-5-amide formaldehyde is allowed to act, with the pyridine-2,5-dicarboxylic acid-5-N-oxymethyl-amide being formed. The formaldehyde can, for example, a formaldehyde-yielding connec tion, z. B. a polymeric formaldehyde (triozymethylene, paraformaldehyde), men entstam. The reaction is preferably carried out in an alkaline medium, since undesirable by-products are easily formed when working below pH 7.

      <I> Example </I> 200 g of pyridine-2,5-dicarboxylic acid-5-amide are slurried in 600 cm3 of water and dilute sodium hydroxide solution 1:10 to p = 9 is added with stirring. The mixture is heated to 80 on the water bath and stirred with 450 cm3 of 361 / o aqueous formaldehyde solution. It is held at 80 for 15 minutes and the hydrogen ion concentration is adjusted to a value of 9-10 using sodium hydroxide solution. Then activated charcoal is added, filtered and neutralized with formic acid exactly to p $ 7. Then acetone is stirred in until a precipitate is formed.

   The same is filtered off with suction after 24 hours and washed with acetone. By vacuum drying at 30 to 40, the sodium salt of pyridine-2,5-dicarboxylic acid-5-N-oxymethyl-amide is obtained as a colorless powder which dissolves up to 20% in cold water with a practically neutral reaction.



  The sodium salt obtained in this way can very easily be precipitated from water with the aid of acetone.



  The free compound can be obtained by carefully acidifying the aqueous solution of a salt of pyridine-2,5-dicarboxylic acid-5-N-oxymethyl-amide. It is a colorless powder that does not show a sharp melting point, but rather slowly decomposes when heated.



  The salts of the new compound are very stable. Your aqueous solutions react almost neutrally and are ideally suited for injections.



  The new compound can see example, easily in the form of their salts, eg. B. of sodium, calcium, or amines, such as diethylamine, diethanolamine, morpholine, etc. isolate. For this purpose, as described in more detail in the example, the salt corresponding to the alkaline condensing agent used can be precipitated by mixing the reaction solution with an organic solvent miscible with Vrasser.


    

Claims (1)

PATENTANSPRUCH Verfahren zur Herstellung eines neuen Aldehydderivates, dadurch gekennzeichnet, dass man auf Pyridin-2,5-dicarbonsäure-5-amid Formaldehyd einwirken lässt. Das so erhaltene Pyridin-2,5-dicarbonsäure-5-N-oxymethyl-amid stellt ein farbloses Pulver dar, das sich beim Erwärmen langsam zersetzt. In verdünnten Alkalien und in Lösungen von Aminen ist die neue Verbindung leicht löslich. Die Verbin dung und namentlich auch ihre löslichen Salze sollen zur Bekämpfung von Infektions krankheiten verwendet werden. UNTERANSPRUCH Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man die Umsetzung in alkalischem Milieu vornimmt. PATENT CLAIM Process for the production of a new aldehyde derivative, characterized in that formaldehyde is allowed to act on pyridine-2,5-dicarboxylic acid-5-amide. The pyridine-2,5-dicarboxylic acid-5-N-oxymethyl-amide thus obtained is a colorless powder which slowly decomposes when heated. The new compound is easily soluble in dilute alkalis and in solutions of amines. The compound and, in particular, its soluble salts are intended to be used to combat infectious diseases. SUBCLAIM Process according to claim, characterized in that the reaction is carried out in an alkaline medium.
CH315083D 1948-05-20 1953-04-25 Process for the preparation of a new aldehyde derivative CH315083A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH266516T 1948-05-20
CH315083T 1953-04-25

Publications (1)

Publication Number Publication Date
CH315083A true CH315083A (en) 1956-07-15

Family

ID=25730908

Family Applications (1)

Application Number Title Priority Date Filing Date
CH315083D CH315083A (en) 1948-05-20 1953-04-25 Process for the preparation of a new aldehyde derivative

Country Status (1)

Country Link
CH (1) CH315083A (en)

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