CH124025A - Process for the preparation of 2-styryl-4-amino-6-ethoxy-quinoline. - Google Patents

Process for the preparation of 2-styryl-4-amino-6-ethoxy-quinoline.

Info

Publication number
CH124025A
CH124025A CH124025DA CH124025A CH 124025 A CH124025 A CH 124025A CH 124025D A CH124025D A CH 124025DA CH 124025 A CH124025 A CH 124025A
Authority
CH
Switzerland
Prior art keywords
styryl
ethoxy
quinoline
amino
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 CH124025A publication Critical patent/CH124025A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D215/38—Nitrogen atoms
    • C07D215/42—Nitrogen atoms attached in position 4

Description

  

  Verfahren     zier    Darstellung von     2-Styryl-4-anzino-6-äthogy-ehinolin.       Es wurde gefunden, dass die bisher un  bekannten     4-Aminochinoline    mit einem un  gesättigten     Substituenten    in     2-Stellung    und  deren Derivate sich durch eine stark     bakte-          ricide    Wirkung auszeichnen und für thera  peutische Zwecke wertvoll sind. Speziell das       2-Styryl-4-amino-6-äthoxy-chinolin    zeigt eine  sehr günstige Wirkung und soll als solches  oder in Form seiner Salze in der Therapie  Verwendung finden.

   Man kann zu der Ver  bindung gelangen, indem man     2-Styryl-4-ha-          logen-6-äthoxy-chinoline    mit Ammoniak um  setzt.  



  Gegenstand dieser Erfindung ist ein Ver  fahren zur Darstellung von     2-Styryl-4-amino-          6-äthoxy-chinolin,    welches darin besteht, dass  man     2-Styryl-4.chlor-6-äthoxy-chinolin    mit  Ammoniak umsetzt.  



  <I>Beispiel:</I>  1 Teil     2-Styryl-4-chlor-6-äthoxy-chinolin     wird mit 10 Teilen 20     o/oigem    alkoholischem  Ammoniak 8 Stunden im Rohr auf 200 bis  220<B>0</B> erhitzt. Die     Aminoverbindung    wird vom    unveränderten Chlorprodukt mittelst kalter,  verdünnter Essigsäure getrennt, aus der essig  sauren Lösung mit Ammoniak gefällt und  aus verdünntem Alkohol umkristallisiert.  Die neue Verbindung schmilzt bei 2121 und  bildet mit Milchsäure,     Glykolsäure    und China  säure in Wasser leichtlösliche Salze.



  Process for the preparation of 2-styryl-4-anzino-6-ethogy-ehinolin. It has been found that the previously unknown 4-aminoquinolines with an unsaturated substituent in the 2-position and their derivatives are characterized by a strong bactericidal effect and are valuable for therapeutic purposes. In particular, 2-styryl-4-amino-6-ethoxy-quinoline has a very beneficial effect and is intended to be used in therapy as such or in the form of its salts.

   The connection can be obtained by converting 2-styryl-4-halo-6-ethoxy-quinolines with ammonia.



  This invention relates to a process for the preparation of 2-styryl-4-amino-6-ethoxy-quinoline, which consists in reacting 2-styryl-4-chloro-6-ethoxy-quinoline with ammonia.



  <I> Example: </I> 1 part of 2-styryl-4-chloro-6-ethoxy-quinoline is mixed with 10 parts of 20% alcoholic ammonia for 8 hours in the tube to 200 to 220 <B> 0 </B> heated. The amino compound is separated from the unchanged chlorine product by means of cold, dilute acetic acid, precipitated from the acetic acid solution with ammonia and recrystallized from dilute alcohol. The new compound melts at 2121 and forms salts with lactic acid, glycolic acid and quinic acid that are easily soluble in water.

Claims (1)

PATENTAIVTSPRÜCH Verfahren zur Darstellung von 2-Styryl- 4-Amino-6-äthoxy-chinolin, dadurch gekenn zeichnet, dass man 2-Styryl-4-chlor-6-äthoxy- chinolin mit Ammoniak umsetzt. Die Verbindung schmilz(: bei 2120 und bildet mit Milchsäure, Glykolsäure und China säure in Wasser leicht lösliche Salze. Sie besitzt eine stark baktericide Wirkung. Die Verbindung soll als solche oder in Form ihrer Salze in der Therapie Verwendung finden. PATENTAIVTSPRÜCH Process for the preparation of 2-styryl-4-amino-6-ethoxy-quinoline, characterized in that 2-styryl-4-chloro-6-ethoxyquinoline is reacted with ammonia. The compound melts (: at 2120 and forms salts easily soluble in water with lactic acid, glycolic acid and quinic acid. It has a strong bactericidal effect. The compound is to be used as such or in the form of its salts in therapy.
CH124025D 1926-09-07 1926-09-07 Process for the preparation of 2-styryl-4-amino-6-ethoxy-quinoline. CH124025A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH124025T 1926-09-07

Publications (1)

Publication Number Publication Date
CH124025A true CH124025A (en) 1928-01-02

Family

ID=4382660

Family Applications (1)

Application Number Title Priority Date Filing Date
CH124025D CH124025A (en) 1926-09-07 1926-09-07 Process for the preparation of 2-styryl-4-amino-6-ethoxy-quinoline.

Country Status (1)

Country Link
CH (1) CH124025A (en)

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