CH315082A - Process for the preparation of a new aldehyde derivative - Google Patents

Process for the preparation of a new aldehyde derivative

Info

Publication number
CH315082A
CH315082A CH315082DA CH315082A CH 315082 A CH315082 A CH 315082A CH 315082D A CH315082D A CH 315082DA CH 315082 A CH315082 A CH 315082A
Authority
CH
Switzerland
Prior art keywords
aldehyde derivative
dicarboxylic acid
pyridine
amide
new
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 CH315082A publication Critical patent/CH315082A/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     Aldehydderi-          vates,    welches gute keimtötende     Eigensehaf-          t.en    besitzt. Die Verbindung und     ha-Liptsäeh-          lieh    auch ihre löslichen Salze sollen zur     Be-'          kämpfung    von Infektionskrankheiten verwen  det     -,verden.     



  Das den Gegenstand des Patentes bildende  Verfahren ist dadurch     gekennzeichnet,    dass  man auf     Pyridin-3,4-dicarbonsäure-3-anid          Fornialdeliy    d einwirken, lässt, wobei sich das       Pvi,idin-3,4-diearbonsäure-3-N-ozymethyl-amid     bildet. Der     Formaldehyd    kann beispielsweise       auch    einer Formaldehyd liefernden Verbin  dung, z. B. einem polymeren Formaldehyd       (Ti-ioxymethylen.,        Paraformaldehyd),    entstam  men. Vorzugsweise wird die Umsetzung in  alkalischem     Milieu    vorgenommen, da beim Ar  beiten unter PH 7 leicht unerwünschte Neben  produkte entstehen.

      200     g        Pyridin-3,4-dicarbonsäure-3-amid     werden in 600 ein?, Wasser aufgeschlämmt und       Unter    Rühren verdünnte Natronlauge 1 :10  bis     pH    = 9 zugesetzt. Man     erwärmt    auf dem       Wasserbad    auf 80  und verrührt mit 450     cm3          36%iger        wässeriger        Formaldehydlösung,        Man     hält 15 Minuten bei 80  und stellt die     )Vasser-          stoffioneiAonzentration    mit Hilfe von Natron  lauge auf einen Wert von 9 bis 10 ein.

   Da  nach setzt man Aktivkohle zu, filtriert und    neutralisiert mit Ameisensäure genau auf       pH    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     Pyri-          din-3,4-dicarbonsäure-3-N-oxymethyl-amids    als  farbloses Pulver, das sich in kaltem Wasser       bis        zu        20%        mit        praktisch        neutraler        Reaktion     löst.

      Das so erhaltene     Natriumsalz    kann sehr  leicht aus Wasser mit Hilfe von Aceton umge  fällt werden. Die freie Verbindung kann durch  vorsichtiges Ansäuern der wässerigen Lösung  eines Salzes des     Pyridin-3,4-dicarbonsäure-3-          N-oxymethyl-amids    erhalten werden. Sie stellt  ein farbloses Pulver dar, das keinen scharfen       Schmelzpunkt    zeigt, sondern sich beim Er  wärmen 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 sich beispiels  weise leicht in Form ihrer Salze, z. B. des  Natriums, Kalziums, oder von Aminen, wie von       Diäthylamin,        Diäthanolamin,        1lorpholin        usw"     isolieren. Zu diesem Zwecke     kann    man,     wie     im Beispiel näher beschrieben, das dem ver  wendeten alkalischen Kondensationsmittel ent  sprechende     Salz    durch Vermischen der Reak-           tionslösung    mit einem organischen, mit Was  ser mischbaren Lösungsmittel ausfällen.



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



  The method forming the subject of the patent is characterized in that pyridine-3,4-dicarboxylic acid-3-anide Fornialdeliy d can act, whereby the Pvi, idine-3,4-dicarboxylic acid-3-N-ozymethyl- amide forms. The formaldehyde can, for example, a formaldehyde-supplying connec tion, z. B. a polymeric formaldehyde (Ti-ioxymethylene., Paraformaldehyde), entstam men. The reaction is preferably carried out in an alkaline medium, since undesirable by-products are easily formed when working below PH 7.

      200 g of pyridine-3,4-dicarboxylic acid 3-amide are suspended in 600 ml of water and dilute sodium hydroxide solution 1:10 to pH = 9 is added with stirring. The mixture is heated to 80 on the water bath and stirred with 450 cm3 of 36% aqueous formaldehyde solution. The temperature is maintained at 80 for 15 minutes and the hydrogen ion concentration is adjusted to a value of 9 to 10 with the aid of sodium hydroxide solution.

   Then activated charcoal is added, filtered and neutralized with formic acid to exactly pH 7. Then acetone is stirred in until a precipitate forms. The same is filtered off with suction after 24 hours and washed with acetone. Vacuum drying at 30 to 40 gives the sodium salt of pyridine-3,4-dicarboxylic acid 3-N-oxymethyl amide as a colorless powder which dissolves in cold water up to 20% with a practically neutral reaction.

      The sodium salt thus obtained can very easily be turned over from water with the aid of acetone. The free compound can be obtained by carefully acidifying the aqueous solution of a salt of pyridine-3,4-dicarboxylic acid-3-N-oxymethyl-amide. It is a colorless powder that does not have a sharp melting point, but slowly decomposes when heated.



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



  The new compound can, for example, easily in the form of their salts, eg. B. of sodium, calcium, or amines, such as diethylamine, diethanolamine, 1lorpholine, etc. "For this purpose, as described in more detail in the example, the salt corresponding to the alkaline condensing agent used can be isolated by mixing the reaction solution with precipitate an organic solvent that is miscible with water.


    

Claims (1)

PATENTANSPRUCH Verfahren zur Herstellung eines neuen Aldehydderivates, dadurch gekennzeichnet, dass man auf Pyridin-3,4-dicarbonsäure-3-amid Formaldehyd einwirken lässt. Das so erhaltene Pyridin-3,4-dica.rbonsäure-3-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 Infektionskrank heiten 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-3,4-dicarboxylic acid-3-amide. The pyridine-3,4-dicarboxylic acid 3-N-oxymethyl-amide thus obtained is a colorless powder which slowly decomposes when heated. It is in dilute alkalis and in solutions of amines. the new compound is easily soluble. The compound and in particular its soluble salts are to be used to combat infectious diseases. SUBSTANTIAL CLAIM Process according to claim, characterized in that the reaction is carried out in an alkaline medium.
CH315082D 1948-05-20 1953-04-25 Process for the preparation of a new aldehyde derivative CH315082A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH266516T 1948-05-20
CH315082T 1953-04-25

Publications (1)

Publication Number Publication Date
CH315082A true CH315082A (en) 1956-07-15

Family

ID=25730907

Family Applications (1)

Application Number Title Priority Date Filing Date
CH315082D CH315082A (en) 1948-05-20 1953-04-25 Process for the preparation of a new aldehyde derivative

Country Status (1)

Country Link
CH (1) CH315082A (en)

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