CH154173A - Process for the preparation of 5,6-dimethoxy-8-aminoquinoline. - Google Patents

Process for the preparation of 5,6-dimethoxy-8-aminoquinoline.

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Publication number
CH154173A
CH154173A CH154173DA CH154173A CH 154173 A CH154173 A CH 154173A CH 154173D A CH154173D A CH 154173DA CH 154173 A CH154173 A CH 154173A
Authority
CH
Switzerland
Prior art keywords
dimethoxy
aminoquinoline
weight
parts
preparation
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellsc Farbenindustrie
Original Assignee
Ig Farbenindustrie 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 Ig Farbenindustrie Ag filed Critical Ig Farbenindustrie Ag
Publication of CH154173A publication Critical patent/CH154173A/en

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

  Verfahren zur Darstellung von     5.6-Dimethoxy-8-aminochinolin.       Gegenstand vorliegender Erfindung ist  ein Verfahren zur     Darstellung    des als Zwi  schenprodukt für     die    Herstellung von Farb  stoffen und     Arzneimitteln    verwendbaren  5 .

   6 -     Dimethoxy-8-aminochinolins,    dadurch  gekennzeichnet, dass man 5 - Halogen - 6     -          nietlioxy-8-nitrochinolin    mit einem     Meta11-          methylat,    insbesondere     Alkalimethylat    be  handelt und das gebildete     5.6-Dimethoxy-          8-nitroehinolin    reduziert.  



  <I>Beispiel:</I>       5.6-Dimetlboxy-8-nitrochinolin:    28,3  Gewichtsteile 5 -Brom - 6 -     methoxy    - 8     -nitro-          chinolin    (F.     20,5    bis 206  ) werden: in einer  Lösung von     2,3        Gewichtsteilen    Natrium in  <B>1600</B> Gewichtsteilen Methylalkohol 6 Stun  den bei<B>130</B> bis 140'     unter    Druck erhitzt.

    Nach dem Erkalten wird das in     Form    langer  Nadeln ausgeschiedene 5 . 6 -     Dimethoxy    - 8     -          nitrochinolin    abgesaugt.     Es,    zeigt den    Schmelzpunkt 126 bis 128  . Die     Ausbeute     beträgt     etwa.    85 %.  



  Die gleiche Verbindung erhält man mit  ähnlicher Ausbeute, wenn man 238 Gewichts  teile     5-Chlor-6-methoxy-8-nitroehinolin    (F.  202 bis! 203  ) mit einer     Lösung    von 1     Mol          Natriummethyla.t    in 4000     Gewichtsteilen     Methylalkohol einige Tage zum Sieden er  hitzt und das Reaktionsprodukt nach dem  Abdampfen des überschüssigen     Methylalho-          hols    wie oben abscheidet.  



  <I>b)</I>     5.6-Dimethoxy-8-aminochi-nolin.   <I>30</I>       Gewichtsteile    5 . 6 -     Dimethoxy-8-nitrocliino-          lin    werden     langsam    in eine siedende Mi  schung von 300 Gewichtsteilen     Eisenmehl.     500 Gewichtsteilen Wasser und 2 Gewichts  teilen     Eisessig    innerhalb drei Stunden ein  getragen.

   Nach Beendigung der     Umsetzung     wird mit     galiumkarbonat    alkalisch gemacht  und die Reaktionsmischung wiederholt     aus-          geäthert.    Aus dem Äther kristallisiert     beim              Tindampfen    das     5.6-Dimethoxy-8-amino-          chinolin    in hellgelben Kristallen vom  Schmelzpunkt 148'     aus.    Die Ausbeute be  trägt 80 bis 90 %.  



  Die Reduktion lässt sich auch mittelst       Zinnchloriir    in     Eisessiglösung    durchführen.



  Process for the preparation of 5,6-dimethoxy-8-aminoquinoline. The present invention relates to a process for the preparation of the 5 which can be used as an intermediate product for the production of dyes and drugs.

   6 - dimethoxy-8-aminoquinoline, characterized in that 5 - halogen - 6 - nietlioxy-8-nitroquinoline is treated with a meta11-methylate, in particular alkali metal methylate, and the 5,6-dimethoxy-8-nitroehinoline formed is reduced.



  <I> Example: </I> 5.6-Dimetlboxy-8-nitroquinoline: 28.3 parts by weight of 5-bromo-6-methoxy-8-nitro-quinoline (F. 20.5 to 206) are: in a solution of 2 , 3 parts by weight of sodium in <B> 1600 </B> parts by weight of methyl alcohol for 6 hours at <B> 130 </B> to 140 'heated under pressure.

    After cooling down, the 5. 6 - dimethoxy - 8 - nitroquinoline sucked off. It shows a melting point of 126 to 128. The yield is about. 85%.



  The same compound is obtained with a similar yield if you boil 238 parts by weight of 5-chloro-6-methoxy-8-nitroehinoline (F. 202 to! 203) with a solution of 1 mol of sodium methyla.t in 4000 parts by weight of methyl alcohol for a few days it heats and, after the excess methyl alcohol has been evaporated off, the reaction product is deposited as above.



  <I> b) </I> 5,6-dimethoxy-8-aminochinoline. <I> 30 </I> parts by weight 5. 6 - Dimethoxy-8-nitrocliino- lin are slowly mixed into a boiling mixture of 300 parts by weight of iron flour. 500 parts by weight of water and 2 parts by weight of glacial acetic acid are worn within three hours.

   After the reaction has ended, it is made alkaline with galium carbonate and the reaction mixture is repeatedly extracted with ether. When evaporating tin, the 5,6-dimethoxy-8-aminoquinoline crystallizes out of the ether in light yellow crystals with a melting point of 148 '. The yield be 80 to 90%.



  The reduction can also be carried out by means of tin chloride in a glacial acetic acid solution.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung von 5 . 6-Di- methoxy-8-aminochinolin, dadurch gekenn zeichnet, dass man 5-Halogen-6-metho-xy-8- nitrochinolin mit einem Metallmethylat be- handelt und das erhaltene 5. 6-Dimethoxy-R- nitrochinolin reduziert. PATENT CLAIM: Method for the representation of 5th 6-Dimethoxy-8-aminoquinoline, characterized in that 5-halo-6-methoxy-8-nitroquinoline is treated with a metal methylate and the 5, 6-dimethoxy-R-nitroquinoline obtained is reduced. Die neue Verbindung bildet hellgelbe Kristalle vom Schmelzpunkt 148 . UNTERANSPRUCH: Verfahren nach Patentanspruch, dadureh gekennzeichnet, dass man als Metallmethy la.t ein Alkalimethylat verwendet. The new compound forms pale yellow crystals with a melting point of 148. SUBClaim: Process according to claim, characterized in that an alkali metal methylate is used as the metal methylate.
CH154173D 1930-02-17 1931-02-10 Process for the preparation of 5,6-dimethoxy-8-aminoquinoline. CH154173A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE154173X 1930-02-17

Publications (1)

Publication Number Publication Date
CH154173A true CH154173A (en) 1932-04-30

Family

ID=5676174

Family Applications (1)

Application Number Title Priority Date Filing Date
CH154173D CH154173A (en) 1930-02-17 1931-02-10 Process for the preparation of 5,6-dimethoxy-8-aminoquinoline.

Country Status (1)

Country Link
CH (1) CH154173A (en)

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