CH157829A - Process for the preparation of 5-methoxy-6-ethoxy-8-aminoquinoline. - Google Patents

Process for the preparation of 5-methoxy-6-ethoxy-8-aminoquinoline.

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Publication number
CH157829A
CH157829A CH157829DA CH157829A CH 157829 A CH157829 A CH 157829A CH 157829D A CH157829D A CH 157829DA CH 157829 A CH157829 A CH 157829A
Authority
CH
Switzerland
Prior art keywords
sep
ethoxy
methoxy
aminoquinoline
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 CH157829A publication Critical patent/CH157829A/en

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Description

  

  Verfahren zur Darstellung von     6-lllethogy-6-äthoxy-8-aminoehinolin.       Gegenstand vorliegender Erfindung ist  ein Verfahren zur Darstellung des als Zwi  schenprodukt für die Herstellung von Farb  stoffen und Arzneimitteln verwendbaren     5-          Methoxy-6-äthoxy-8-aminochinolins,    dadurch  gekennzeichnet, dass man     5-Halogen-6-          äthoxy-8-nitrochinolin    mit einem     Metall-          methy        lat,    vorzugsweise     Alkalimethylat    be  handelt und das gebildete     5-Methoxy-6-          äthoxy-8-nitrochinolin    reduziert.

      <I>Beispiel:</I>    295 Gewichtsteile     5-Brom-6-äthoxy-8-ni-          trochinolin    (F. 176 bis 177  ) werden     in    einer  Lösung von 23 Gewichtsteilen Natrium in  <B>1600</B> Gewichtsteilen Methylalkohol 6 Stun  den bei 130 bis 1-0   unter     Druck    erhitzt.  Nach dem Erkalten wird das in Form langer  Nadeln ausgeschiedene     5-Methoxy-6-äthoxy-          8-nitrochinolin    abgesaugt. Es zeigt den    Schmelzpunkt 86 bis 87  .

   Die Ausbeute be  trägt etwa 85     %.    30 Gewichtsteile des     5-Me-          thoxy-6-äthoxy-8-nitrochinolins    werden lang  sam in eine siedende Mischung von 300 Ge  wichtsteilen Eisenmehl, 500 Gewichtsteilen  Wasser und 2 Gewichtsteilen Eisessig inner  halb 3 Stunden eingetragen. Nach Beendi  gung der Umsetzung wird mit     Kaliumkarbo-          nat    alkalisch gemacht und die Reaktions  mischung wiederholt     ausgeäthert.    Aus dem  Äther kristallisiert beim Eindampfen das     5-          Methoxy-6-äthoxy-8-aminochinolin    in hell  gelben Kristallen vom Schmelzpunkt 119  .  Die Ausbeute beträgt 80 bis<B>90%.</B>



  Process for the preparation of 6-lllethogy-6-ethoxy-8-aminoehinoline. The present invention is a process for the preparation of the inter mediate product for the production of dyes and drugs usable 5-methoxy-6-ethoxy-8-aminoquinoline, characterized in that 5-halo-6-ethoxy-8-nitroquinoline with a metal methylate, preferably alkali metal, and the 5-methoxy-6-ethoxy-8-nitroquinoline formed is reduced.

      <I> Example: </I> 295 parts by weight of 5-bromo-6-ethoxy-8-nitroquinoline (F. 176 to 177) are in a solution of 23 parts by weight of sodium in 1600 parts by weight of methyl alcohol Heated for 6 hours at 130 to 1-0 under pressure. After cooling, the 5-methoxy-6-ethoxy-8-nitroquinoline excreted in the form of long needles is suctioned off. It shows a melting point of 86 to 87.

   The yield is about 85%. 30 parts by weight of 5-methoxy-6-ethoxy-8-nitroquinoline are slowly introduced 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 within 3 hours. When the reaction has ended, it is made alkaline with potassium carbonate and the reaction mixture is repeatedly extracted with ether. On evaporation, the 5-methoxy-6-ethoxy-8-aminoquinoline crystallizes from the ether in light yellow crystals with a melting point of 119. The yield is 80 to <B> 90%. </B>

Claims (1)

PA TENTANSPRTTCH Verfahren zur Darstellung von 5-Me- thoxy-6-Äthoxy-8-aminochinolin, dadurch ge kennzeichnet, dass man 5-Halogen-6-äthoxy- 8-nitrochinolin mit einem Metallmethylat be- handelt und das gebildete 5-Methoxy-6- äthogy-8-nitrochinolin reduziert. Das neue Produkt bildet hellgelbe Kri stalle vom Schmelzpunkt 119 . EMI0002.0003 UNTERANSPRUCH <tb> Verfahren <SEP> nach <SEP> Patentanspruch, <SEP> (l@iilurcb <tb> gekennzeichnet, <SEP> dass <SEP> man <SEP> als <SEP> Metallinethvlat <tb> ein <SEP> Alkalimethylat <SEP> verwendet. PA TENTANSPRTTCH Process for the preparation of 5-methoxy-6-ethoxy-8-aminoquinoline, characterized in that 5-halo-6-ethoxy-8-nitroquinoline is treated with a metal methylate and the 5-methoxy- 6- Ethogy-8-nitroquinoline reduced. The new product forms light yellow crystals with a melting point of 119. EMI0002.0003 SUBClaim <tb> Method <SEP> according to <SEP> patent claim, <SEP> (l @ iilurcb <tb> marked, <SEP> that <SEP> man <SEP> as <SEP> Metallinethvlat <tb> an <SEP> alkali methylate <SEP> is used.
CH157829D 1930-02-17 1931-02-10 Process for the preparation of 5-methoxy-6-ethoxy-8-aminoquinoline. CH157829A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE157829X 1930-02-17
CH154173T 1931-02-10

Publications (1)

Publication Number Publication Date
CH157829A true CH157829A (en) 1932-10-15

Family

ID=25716376

Family Applications (1)

Application Number Title Priority Date Filing Date
CH157829D CH157829A (en) 1930-02-17 1931-02-10 Process for the preparation of 5-methoxy-6-ethoxy-8-aminoquinoline.

Country Status (1)

Country Link
CH (1) CH157829A (en)

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