CH338190A - Process for the preparation of a novel derivative of isonicotinyl hydrazide - Google Patents

Process for the preparation of a novel derivative of isonicotinyl hydrazide

Info

Publication number
CH338190A
CH338190A CH338190DA CH338190A CH 338190 A CH338190 A CH 338190A CH 338190D A CH338190D A CH 338190DA CH 338190 A CH338190 A CH 338190A
Authority
CH
Switzerland
Prior art keywords
isonicotinyl
preparation
novel derivative
hydrazide
isonicotinyl hydrazide
Prior art date
Application number
Other languages
French (fr)
Inventor
Michel Jacob Robert
Liakhoff Leonide
Original Assignee
Rhone Poulenc Chemicals
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 Rhone Poulenc Chemicals filed Critical Rhone Poulenc Chemicals
Publication of CH338190A publication Critical patent/CH338190A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic 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
    • C07D213/02—Heterocyclic 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
    • C07D213/04—Heterocyclic 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
    • C07D213/60—Heterocyclic 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/86—Hydrazides; Thio or imino analogues thereof

Landscapes

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

Description

  

  Procédé de     préparation    d'un nouveau dérivé de     l'isonicotiny1hydrazide       La présente invention a pour objet un procédé de préparation d'un nouveau dérivé de     l'isonicotinyl-          hydrazide,    à savoir l'     (isonicotinyl-2'-hydrazino-1')-1-phényl-3-propane-disulfonate    de sodium de formule  
EMI0001.0006     
    Ce     procédé    est caractérisé en ce que l'on fait  réagir du bisulfite de sodium sur     l'isonicotinylhydra-          zone    de l'aldéhyde cinnamique.  



  Le produit obtenu     conserve    les propriétés anti  bactériennes de     l'isonicotinylhydrazide    tout en étant  nettement moins toxique.  



  <I>Exemple</I>  12,5 g     d'isonicotinyl-1-cinnamylidène-2-hydra-          zine    sont ajoutés à 22,6     cm3    d'une lessive de     bisulfite     de sodium à 460 g par litre. On agite pendant 1 h. 30  au bain-marie bouillant, laisse refroidir et essore la  masse obtenue. Le produit essoré est     repris    par  70     cm,'    d'eau à température ordinaire ; on filtre l'in  soluble qui est de     l'hydrazone    de départ et ajoute  375     cm-'    d'acétone au filtrat.

   Il cristallise un produit    qu'on essore, lave et sèche à     poids    constant sous  vide en     présence    d'acide     sulfurique.    Il présente les  valeurs     analytiques    suivantes :     o/o    N = 8,35 ;     o/o    S =       12,45    ;     o/o        Na        =        8,85    ;

       %        H20        =        9,6.        Les        valeurs     théoriques pour un produit cristallisé avec 3     molé-          cules        d'eau        sont:        %        N        =        8,18    ;     %        S        =        12,45    ;

          /o        Na        =        8,97    ;     %        H20        =        10,5.  



  Process for preparing a new derivative of isonicotinylhydrazide The present invention relates to a process for preparing a new derivative of isonicotinyl-hydrazide, namely (isonicotinyl-2'-hydrazino-1 ') - Sodium 1-phenyl-3-propane-disulfonate of the formula
EMI0001.0006
    This process is characterized in that sodium bisulfite is reacted with the isonicotinyl hydra-zone of cinnamic aldehyde.



  The product obtained retains the anti-bacterial properties of isonicotinyl hydrazide while being significantly less toxic.



  <I> Example </I> 12.5 g of isonicotinyl-1-cinnamylidene-2-hydrazine are added to 22.6 cm3 of sodium bisulfite lye at 460 g per liter. Stirred for 1 h. 30 in a boiling water bath, leave to cool and wring out the resulting mass. The drained product is taken up in 70 cm 3 of water at ordinary temperature; the insoluble matter, which is the starting hydrazone, is filtered off and 375 cm 3 of acetone are added to the filtrate.

   It crystallizes a product which is filtered off, washed and dried at constant weight under vacuum in the presence of sulfuric acid. It presents the following analytical values: o / o N = 8.35; o / o S = 12.45; o / o Na = 8.85;

       % H2O = 9.6. Theoretical values for a product crystallized with 3 molecules of water are:% N = 8.18; % S, 12.45;

          / o Na = 8.97; % H2O = 10.5.

Claims (1)

REVENDICATION Procédé de préparation de l' (isonicotinyl-2'- hydrazino-l')-1-phényl-3-propane-disulfonate de so dium, caractérisé en ce que l'on fait réagir du bisul- fite de sodium sur l'isonicotinylhydrazone de l'aldé hyde. cinnamique. CLAIM Process for preparing sodium (isonicotinyl-2'-hydrazino-l ') - 1-phenyl-3-propane-disulfonate, characterized in that sodium bisulphite is reacted with isonicotinylhydrazone of aldehyde. cinnamic.
CH338190D 1954-12-01 1955-11-28 Process for the preparation of a novel derivative of isonicotinyl hydrazide CH338190A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR338190X 1954-12-01

Publications (1)

Publication Number Publication Date
CH338190A true CH338190A (en) 1959-05-15

Family

ID=8891553

Family Applications (1)

Application Number Title Priority Date Filing Date
CH338190D CH338190A (en) 1954-12-01 1955-11-28 Process for the preparation of a novel derivative of isonicotinyl hydrazide

Country Status (1)

Country Link
CH (1) CH338190A (en)

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