CH304314A - Process for the preparation of a new quinoxaline. - Google Patents

Process for the preparation of a new quinoxaline.

Info

Publication number
CH304314A
CH304314A CH304314DA CH304314A CH 304314 A CH304314 A CH 304314A CH 304314D A CH304314D A CH 304314DA CH 304314 A CH304314 A CH 304314A
Authority
CH
Switzerland
Prior art keywords
sep
preparation
formula
new
quinoxaline
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellschaft Ciba
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 CH304314A publication Critical patent/CH304314A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
    • C07D471/14—Ortho-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Description

  

  verfahren     zur        Herstellung        eines    neuen     Chinoxalins.       Gegenstand des vorliegenden Patentes ist  ein Verfahren zur     Herstellung    eines neuen       Chinoxa.lins,    welches dadurch gekennzeichnet  ist, dass man eine Verbindung der Formel  
EMI0001.0007     
          orin    X und F bei der Reaktion sich abspal  tende Reste bedeuten, mit einer die Atomgrup  pierung     =N-CH2-CH2-N=    aufweisenden  Verbindung umsetzt.  



  Das so erhaltene     5,6,7,8-Dipyrido-(5',6',-          5",6")-1,2,3,=1-tetrahydro-ehinoxalin    der For  mel  
EMI0001.0012     
    schmilzt bei 171 . Es besitzt     Anti-Virus-Wir-          kuiigund    soll als Heilmittel Verwendung fin  den. So zeigt es sich besonders wirksam gegen  dem     Influenza-Virus    im Hühnerembryo.    Als Ausgangsstoffe verwendet man vorteil  haft einerseits     1,7-Phenanthrolin-5,6-chinon     und anderseits     Äthylendiamin-    (1,2) oder       Äthylenharnstoff.    Das     Äthylendiamin    kann  auch in Form seiner Salze verwendet werden.

    Die Reaktion wird zweckmässig in Anwesenheit  eines Verdünnungsmittels     durchgeführt.    Das  als Ausgangsstoff     verwendete        1,7-Phenanthro-          lin-5,6-chinon    kann nach dem Verfahren des       schweiz.    Patentes Nr. 296570 hergestellt wer  den.  



  <I>Beispiel:</I>  5 Gewichtsteile     1,7-Phenanthrolin-5,6-chi-          non    werden in 300     Volumteilen        abs.        Äthyl-          alkohol    gelöst und heiss     mit    1,5     Gewichtsteilen          "ithylendiamin    versetzt. Die Reaktion tritt so  fort unter     Farbumschlag    ein.

   Dabei bildet sich  sehr wahrscheinlich zunächst das     5,6,7,8-Di-          pyrido    - (5',6',5",6") -     dihydro    -     chinoxalin    der  Formel  
EMI0001.0039     
    Man dampft auf 80     Volumteile    ein.

   Das aus  gefallene     5,6,7,8-Dipyrido-    (5',6',5",6") -chin-           oxalin        zeigt    nach dem     Umkristallisieren    aus  Methanol einen F. von     302-3030.    Formel  
EMI0002.0005     
  
EMI0002.0006     
  
    Durch <SEP> weiteres <SEP> Einengen <SEP> der <SEP> Mutterlauge
<tb>  kann <SEP> das <SEP> 5,6,7,8-Dipyrido-(5',6',5",6")-1,2,3,-1  i.etrahvdro-eliinoxalin <SEP> der <SEP> Formel     
EMI0002.0007     
    gewonnen     werden:    es     sehmilzt    bei 171



  process for the production of a new quinoxaline. The subject of the present patent is a process for the preparation of a new quinoxa.lin, which is characterized in that a compound of the formula
EMI0001.0007
          orin X and F denote residues that split off during the reaction, with a compound having the atom group = N-CH2-CH2-N =.



  The 5,6,7,8-dipyrido (5 ', 6', -5 ", 6") - 1,2,3, = 1-tetrahydro-ehinoxaline of the formula obtained in this way
EMI0001.0012
    melts at 171. It has anti-virus properties and is said to be used as a remedy. It is particularly effective against the influenza virus in the chicken embryo. The starting materials used are advantageous on the one hand 1,7-phenanthroline-5,6-quinone and on the other hand ethylenediamine (1,2) or ethylene urea. The ethylenediamine can also be used in the form of its salts.

    The reaction is expediently carried out in the presence of a diluent. The 1,7-phenanthroline-5,6-quinone used as the starting material can be produced using the Swiss method. Patent No. 296570 produced who the.



  <I> Example: </I> 5 parts by weight of 1,7-phenanthroline-5,6-quinone in 300 parts by volume of abs. Dissolve ethyl alcohol and add 1.5 parts by weight of ethylenediamine while hot. The reaction occurs immediately with a color change.

   The 5,6,7,8-dipyrido (5 ', 6', 5 ", 6") - dihydro - quinoxaline of the formula is very likely to be formed first
EMI0001.0039
    It is evaporated to 80 parts by volume.

   The 5,6,7,8-dipyrido (5 ', 6', 5 ", 6") -quinoxaline which has precipitated has an F. of 302-3030 after recrystallization from methanol. formula
EMI0002.0005
  
EMI0002.0006
  
    By <SEP> further <SEP> concentration <SEP> of the <SEP> mother liquor
<tb> <SEP> can <SEP> 5,6,7,8-dipyrido- (5 ', 6', 5 ", 6") - 1,2,3, -1 i.etrahvdro-eliinoxalin <SEP > the <SEP> formula
EMI0002.0007
    be obtained: it sehmelzt at 171

Claims (1)

EMI0002.0010 P <SEP> ATENTANSPRL?CH: <tb> Verfahren <SEP> zur <SEP> Herstellung <SEP> eines <SEP> neuen <tb> Chino-alins, <SEP> dadureh <SEP> gekennzeiehnet, <SEP> dass <tb> man <SEP> eine <SEP> Verbindung <SEP> der <SEP> Formel EMI0002.0011 EMI0002.0012 worin <SEP> X <SEP> und <SEP> Y <SEP> bei <SEP> der <SEP> Reaktion <SEP> sieh <SEP> abspal tende <SEP> Reste <SEP> bedeuten, <SEP> mit, <SEP> einer <SEP> die <SEP> Atomgrup pierung <SEP> =N-CII@-CH@---N= <SEP> aufweisenden <tb> Verbindunz <SEP> umsetzt. <tb> Das <SEP> so <SEP> erhaltene <SEP> 5,6,7,8-I)ipyrido-(5',6', <tb> )",6"i-1,2,3,-1-tetraliy-dro-eliiiiozaliii <SEP> der <SEP> Por inel EMI0002.0013 sehmilzt bei 171 . EMI0002.0010 P <SEP> ATENTANSPRL? CH: <tb> Procedure <SEP> for <SEP> production <SEP> of a <SEP> new one <tb> Chino-alins, <SEP> dadureh <SEP> marked, <SEP> that <tb> man <SEP> a <SEP> connection <SEP> of the <SEP> formula EMI0002.0011 EMI0002.0012 where <SEP> X <SEP> and <SEP> Y <SEP> for <SEP> the <SEP> reaction <SEP> see <SEP> mean <SEP> split off <SEP> residues, <SEP> with, <SEP > a <SEP> having the <SEP> atom group <SEP> = N-CII @ -CH @ --- N = <SEP> <tb> connection <SEP> implemented. <tb> The <SEP> so <SEP> obtained <SEP> 5,6,7,8-I) ipyrido- (5 ', 6', <tb>) ", 6" i-1,2,3, -1-tetraliy-dro-eliiiiozaliii <SEP> der <SEP> Por inel EMI0002.0013 sehmilzt at 171. Es besitzt Anti-Virus-Wir- kung und soll als Heilmittel Verwendung fin den. UNTERANSPRÜCHE 1. Verfahren naeh Patentansprueh, da durch gekennzeiehnet, dass man 1.,7-Phen- anthrolin-5,6-ehinon als Ausgangsstoff ver- wendet. 2. It has anti-virus effects and is said to be used as a remedy. SUBClaims 1. Process according to patent claim, as it is marked by the fact that 1., 7-phenanthroline-5,6-ehinone is used as the starting material. 2. Verfahren naeh Patentansprueh und Unteransprueh 1, dadureh gekennzeichnet, dass man mit Äthy-lendiamin-(1,2) umsetzt. Method according to patent claim and sub-claim 1, characterized in that it is reacted with ethylenediamine- (1,2).
CH304314D 1950-05-05 1950-05-05 Process for the preparation of a new quinoxaline. CH304314A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH304314T 1950-05-05
CH301251T 1950-05-05

Publications (1)

Publication Number Publication Date
CH304314A true CH304314A (en) 1954-12-31

Family

ID=25734317

Family Applications (1)

Application Number Title Priority Date Filing Date
CH304314D CH304314A (en) 1950-05-05 1950-05-05 Process for the preparation of a new quinoxaline.

Country Status (1)

Country Link
CH (1) CH304314A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3169317A (en) * 1961-08-16 1965-02-16 Braun Ag Screening or shearing foils for dry-shaving appliances

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3169317A (en) * 1961-08-16 1965-02-16 Braun Ag Screening or shearing foils for dry-shaving appliances

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