CH305347A - Process for the preparation of a therapeutically valuable compound of the quinoline series. - Google Patents

Process for the preparation of a therapeutically valuable compound of the quinoline series.

Info

Publication number
CH305347A
CH305347A CH305347DA CH305347A CH 305347 A CH305347 A CH 305347A CH 305347D A CH305347D A CH 305347DA CH 305347 A CH305347 A CH 305347A
Authority
CH
Switzerland
Prior art keywords
quinoline
methyl
preparation
dimethoxy
therapeutically valuable
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellschaft Farbe Bayer
Original Assignee
Bayer 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 Bayer Ag filed Critical Bayer Ag
Publication of CH305347A publication Critical patent/CH305347A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

  

  Verfahren zur Herstellung einer therapeutisch wertvollen     Verbindung    der     Chinolinreihe.       Gegenstand des vorliegenden Patentes ist  ein Verfahren zur Herstellung einer therapeu  tisch wertvollen Verbindung der     Chinolin-          reihe,    das dadurch gekennzeichnet ist, dass  man     2-Methyl-4-oxy-6,7-dimethoxy-chinolin     mit einem     Allylhalogenid        veräthert,    den so er  haltenen Äther durch Erhitzen in     2-Methyl-3-          allyl-4-oxy-6,7-dimethoxy-chinolin    umlagert  und dieses durch Einwirkung einer Säure zum       2-Methyl-6,

  7-dimethoxy-furanochinolin    der  Formel  
EMI0001.0011     
         cyclisiert.     Die neue Verbindung soll als Arzneimittel  sowie als Zwischenprodukt zur Herstellung  solcher Verwendung finden.  



  <I>Beispiel:</I>  117,4 g     2-Methyl-4-oxy-6,7-dimethoxy-chi-          nolin    werden in 200     cm3    absolutem     Alkohol     suspendiert, mit einer     Allioholatlösung    aus  13g Natrium in 200     cm3        Alkohol    versetzt,  69 g     Allylbromid    eingetropft und 3 Stunden  gekocht. Man destilliert den     Alkohol    mit Was  serdampf ab, setzt etwas Natronlauge zu und  kühlt ab. Das     2-Methyl-4-allyloxy-6,7-dimeth-          oxy-chinolin    scheidet sich in farblosen Kri  stallen vom Schmelzpunkt 97  ab.

   Zur Um-         lagerung    werden 122,6 g dieses Produktes in  500     cm3    a -     Chlornaphthalin    5 Stunden im  Stickstoffstrom auf 200      erwärmt.    Nach Ab  kühlen und Zusatz von Äther kristallisiert  das     2-Methyl-3-allyl-4-oxy-6,7-dimethoxy-chi-          nolin    mit einem Schmelzpunkt von 209  aus.  50 g hiervon werden mit 250     cm3    Bromwasser  stoffsäure (d = 1,7) 20     Stunden        digeriert.     Man löst in Wasser, macht     alkalisch    und schüt  telt mit     Methylenchlorid    aus. Nach Verdamp  fen des Lösungsmittels wird destilliert.

   KP . 0,4  190 . Das     Pikrat    schmilzt bei 231 .  



  Das     2-Methyl-4-oxy-6,7-dimethoxy-chinolin     wird wie folgt hergestellt  165,3 g     Aminoveratrol    und 141 g     Acet-          essigester    wurden in 600     cm3    Benzol mit  2 Tropfen konzentrierter     Salzsäure    gekocht,  bis kein Wasser mehr abgeschieden     wird          (Wasserabscheider).    Der nach dem Verdamp  fen des Benzols verbleibende Rückstand wird  bei 250  in 600     cm3    Chlornaphthalin einge  tropft. Nach Erkalten wird abgesaugt und  mit     Petroläther    gewaschen. Das Reaktionspro  dukt schmilzt bei 283 .



  Process for the preparation of a therapeutically valuable compound of the quinoline series. The subject of the present patent is a process for the preparation of a therapeutically valuable compound of the quinoline series, which is characterized in that 2-methyl-4-oxy-6,7-dimethoxy-quinoline is etherified with an allyl halide that is obtained in this way Ether rearranged by heating in 2-methyl-3-allyl-4-oxy-6,7-dimethoxy-quinoline and this by the action of an acid to 2-methyl-6,

  7-dimethoxy-furanoquinoline of the formula
EMI0001.0011
         cyclized. The new compound is said to be used as a drug and as an intermediate for the production of such use.



  <I> Example: </I> 117.4 g of 2-methyl-4-oxy-6,7-dimethoxy-quinoline are suspended in 200 cm3 of absolute alcohol, mixed with an alliolate solution of 13 g of sodium in 200 cm3 of alcohol, 69 g of allyl bromide added dropwise and boiled for 3 hours. The alcohol is distilled off with water vapor, some sodium hydroxide solution is added and the mixture is cooled. The 2-methyl-4-allyloxy-6,7-dimethoxy-quinoline separates out in colorless crystals with a melting point of 97.

   For the rearrangement, 122.6 g of this product are heated in 500 cm3 of a-chloronaphthalene to 200 for 5 hours in a stream of nitrogen. After cooling off and adding ether, the 2-methyl-3-allyl-4-oxy-6,7-dimethoxyquinoline crystallizes with a melting point of 209. 50 g of this are digested with 250 cm3 of hydrobromic acid (d = 1.7) for 20 hours. Dissolve in water, make alkaline and shake out with methylene chloride. After evaporation of the solvent, it is distilled.

   KP. 0.4 190. The picrate melts at 231.



  The 2-methyl-4-oxy-6,7-dimethoxy-quinoline is prepared as follows 165.3 g of aminoveratrol and 141 g of acetic acid ester were boiled in 600 cm3 of benzene with 2 drops of concentrated hydrochloric acid until no more water is separated out ( Water separator). The residue remaining after evaporation of the benzene is added dropwise at 250 to 600 cm3 of chloronaphthalene. After cooling, it is filtered off with suction and washed with petroleum ether. The reaction product melts at 283.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung einer therapeu tisch wertvollen Verbindung der Chinolin- reihe, dadurch gekennzeichnet, dass man 2-Me- thyl-4-oxy-6,7-dimethoxy-chinolin mit einem Allylhalogenid veräthert, den so erhaltenen Äther durch Erhitze: PATENT CLAIM: Process for the production of a therapeutically valuable compound of the quinoline series, characterized in that 2-methyl-4-oxy-6,7-dimethoxy-quinoline is etherified with an allyl halide, the ether thus obtained by heating: in 2-Methyl-3-allyl-4- oxy-6,7-dimethoxy-chinolin umlagert und die- ses durch Einwirkung einer Säure zum 2-Me- thyl-6,7-dimethoxy-furanochinolin. der Formel EMI0002.0006 cy clisiert. Die neue Verbindung hat den Kp. 0,4 190 bis 200 , ihr Pikrat schmilzt bei 231 . rearranged in 2-methyl-3-allyl-4-oxy-6,7-dimethoxy-quinoline and this by the action of an acid to 2-methyl-6,7-dimethoxy-furanoquinoline. the formula EMI0002.0006 cy clized. The new compound has a bp 0.4 190 to 200, its picrate melts at 231.
CH305347D 1950-05-24 1951-04-30 Process for the preparation of a therapeutically valuable compound of the quinoline series. CH305347A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE305347X 1950-05-24
CH298680T 1951-04-30

Publications (1)

Publication Number Publication Date
CH305347A true CH305347A (en) 1955-02-15

Family

ID=25734026

Family Applications (1)

Application Number Title Priority Date Filing Date
CH305347D CH305347A (en) 1950-05-24 1951-04-30 Process for the preparation of a therapeutically valuable compound of the quinoline series.

Country Status (1)

Country Link
CH (1) CH305347A (en)

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