CH313320A - Process for making a pyridazone - Google Patents

Process for making a pyridazone

Info

Publication number
CH313320A
CH313320A CH313320DA CH313320A CH 313320 A CH313320 A CH 313320A CH 313320D A CH313320D A CH 313320DA CH 313320 A CH313320 A CH 313320A
Authority
CH
Switzerland
Prior art keywords
phenyl
pyridazon
pyridazone
ammonia
making
Prior art date
Application number
Other languages
German (de)
Inventor
Jean Dr Druey
Albrecht Dr Hueni
Heinrich Dr Ringier Beat
Alex Dr Staehelin
Original Assignee
Ciba Geigy
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 Ciba Geigy filed Critical Ciba Geigy
Publication of CH313320A publication Critical patent/CH313320A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
    • C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
    • C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members 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
    • C07D237/22—Nitrogen and oxygen atoms

Description

  

  Verfahren zur Herstellung eines     Pyridazons            (legenstand    des vorliegenden Patentes ist  ein Verfahren zur Herstellung von     5,6-Di-          amino-2-phenyl-pyridazon-(3)    der Formel  
EMI0001.0005     
    Die neue Verbindung wird erhalten, wenn  man     2-Phenyl-pyridazon-(3),    das in 5- und in       6-Stellung    je einen austauschfähigen     Substi-          tuenten    aufweist, mit Ammoniak umsetzt. Diese       Umsetzung    kann auch stufenweise durchge  führt werden.

   Ein austauschfähiger     Substi-          tuent    ist zum Beispiel ein Halogen-, insbeson  dere ein Chloratom, oder auch eine substi  tuierte     Oxy-,    wie     Phenoxy-,    oder     Merca.pto-,     wie     1Iethylmercaptogruppe.     



  Die Reaktion kann in An- oder Abwesen  heit von Verdünnungsmitteln und/oder Kon  densationsmitteln und/oder Katalysatoren im  offenen oder geschlossenen Gefäss unter Druck  durchgeführt werden. So kann man zum Bei  spiel 2     -Pheny    l - 5,6     -dihalogen-        pyridazon    - (3 ),  insbesondere     2-Phenyl-5,6-dichlor-pyridazon-          (3),    im geschlossenen Gefäss in Gegenwart von  Kupfer bei höherer Temperatur mit einer  wässerigen     Ammoniaklösung    umsetzen.    Das Verfahrensprodukt, das     5,6-Diamino-          2-phenyl-pyridazon-(3)    vom F. = 263-265        (Zers.),    ist neu.

   Es soll als Heilmittel oder  als Zwischenprodukt zur Herstellung von  Heilmitteln Verwendung finden.  



  Die Erfindung wird im nachfolgenden  Beispiel näher beschrieben. Zwischen     Ge-          wiehtsteil    und     Volumteil    besteht die gleiche  Beziehung wie zwischen Gramm und Kubik  zentimeter.  



       Beispiel     40 Gewichtsteile     2-Phenyl-5,6-dichlor-pyrid-          azon-(3)    werden mit 200     Volumteilen        konz.     wässerigem Ammoniak, 200     Volumteilen    Was  ser und 1     Gewiehtsteil    Kupferbronze im ge  schlossenen Gefäss 10 Stunden auf 150-165   erhitzt. Nach dem Erkalten     nutscht    man ab,  wäscht den Rückstand mit Wasser, trocknet  ihn und kristallisiert ihn aus wässerigem Al  kohol. Das so erhaltene     5,6-Diamino-2-phenyl-          pyridazon-(3)    schmilzt bei 263-265      (Zers.).  



  Process for the preparation of a pyridazone (reference of the present patent is a process for the preparation of 5,6-di-amino-2-phenyl-pyridazon- (3) of the formula
EMI0001.0005
    The new compound is obtained when 2-phenyl-pyridazon- (3), which has an exchangeable substituent in both the 5- and 6-positions, is reacted with ammonia. This implementation can also be carried out in stages.

   An exchangeable substituent is, for example, a halogen, in particular a chlorine atom, or a substituted oxy, such as phenoxy, or mercapto, such as ethylmercapto group.



  The reaction can be carried out in the presence or absence of diluents and / or condensation agents and / or catalysts in an open or closed vessel under pressure. For example, 2-phenyl-5,6-dihalogen-pyridazon- (3), especially 2-phenyl-5,6-dichloropyridazon- (3), in a closed vessel in the presence of copper at a higher temperature react with an aqueous ammonia solution. The product of the process, the 5,6-diamino-2-phenyl-pyridazon- (3) with a melting point of 263-265 (decomp.), Is new.

   It is said to be used as a remedy or as an intermediate in the manufacture of remedies.



  The invention is described in more detail in the following example. There is the same relationship between the weight part and the volume part as there is between grams and cubic centimeters.



       Example 40 parts by weight of 2-phenyl-5,6-dichloro-pyrid- azon- (3) are concentrated with 200 parts by volume. aqueous ammonia, 200 parts by volume of water and 1 part by weight of copper bronze in a closed vessel heated to 150-165 for 10 hours. After cooling, it is suction filtered, the residue is washed with water, dried and crystallized from aqueous alcohol. The 5,6-diamino-2-phenyl-pyridazon- (3) obtained in this way melts at 263-265 (dec.).

Claims (1)

PATENTANSPRUCH Verfahren zur Herstellung eines Pyrid- azons, dadurch gekennzeichnet, dass man 2-Phenyl-pyridazon-(3), das in 5- und in 6- Stellung je einen austauschfähigen Substi- tuenten aufweist, mit Ammoniak umsetzt. Das Verfahrensprodukt, das 5,6-Diamino- 2-phenyl-pyridazon-(3) vom F. = 263-265 , ist neu. PATENT CLAIM Process for the production of a pyridazone, characterized in that 2-phenyl-pyridazon- (3), which has an exchangeable substituent in each of the 5- and 6-positions, is reacted with ammonia. The product of the process, the 5,6-diamino-2-phenyl-pyridazon- (3) from F. = 263-265, is new. Es soll als Zwischenprodukt zur Her stellung von Heilmitteln Verwendung finden, <B>UNTER-ANSPRÜCHE</B> 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man 2-Phenyl-5,6- dihalogen-pyridazon- (3) mit Ammoniak um setzt. 2. Verfahren nach Patentanspruch und Unteranspruch 1, dadurch gekennzeichnet, dass man 2-Phenyl-5,6-dichlor-pyridazon-(3) mit Ammoniak umsetzt. It is intended to be used as an intermediate for the manufacture of medicinal products, <B> SUB-CLAIMS </B> 1. Process according to patent claim, characterized in that 2-phenyl-5,6-dihalogen-pyridazon- (3) is used Ammonia implements. 2. The method according to claim and dependent claim 1, characterized in that 2-phenyl-5,6-dichloro-pyridazon- (3) is reacted with ammonia. 3. Verfahren nach Patentanspruch und Unteransprüchen 1 und 2, dadurch gekenn zeichnet, da.ss man die Umsetzung in Gegen- wart eines Katalysators durchführt. 3. The method according to claim and dependent claims 1 and 2, characterized in that the reaction is carried out in the presence of a catalyst.
CH313320D 1952-06-20 1953-04-02 Process for making a pyridazone CH313320A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH310245T 1952-06-20
CH313320T 1953-04-02

Publications (1)

Publication Number Publication Date
CH313320A true CH313320A (en) 1956-03-31

Family

ID=25735646

Family Applications (1)

Application Number Title Priority Date Filing Date
CH313320D CH313320A (en) 1952-06-20 1953-04-02 Process for making a pyridazone

Country Status (1)

Country Link
CH (1) CH313320A (en)

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