CH127650A - 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
CH127650A
CH127650A CH127650DA CH127650A CH 127650 A CH127650 A CH 127650A CH 127650D A CH127650D A CH 127650DA CH 127650 A CH127650 A CH 127650A
Authority
CH
Switzerland
Prior art keywords
styryl
quinoline
ethoxy
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 CH127650A publication Critical patent/CH127650A/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

Landscapes

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

Description

  

  Verfahren     zur    Darstellung von     2-Styiyl-4-amino-6-äthogy-chinolin.       Gegenstand dieser Erfindung ist ein Ver  fahren zur Darstellung von     2-Styryl-4-amino-          6-äthoxy-chinolin,    dadurch gekennzeichnet,  dass man     2-Styryl        4-carbazido-6-äthoxy-chino-          lin    mit einem Alkohol erhitzt und das ent  standene     Urethan    mit verseifenden Mitteln  behandelt. Das     2-Styryl-4-amino-6-äthöxy-          chinolin    besitzt stark bakterizide Wirkung  und soll in Form seiner Salze in der Therapie  Verwendung finden.  



  <I>Beispiel</I>       2-Styryl-6-äthoxy-        chinolin-4-carbonsäure-          äthylester    wird durch Erhitzen mit über  schüssigem wasserfreiem     Hydrazin    in alko  holischer Lösung in das     4-Hydrazid    über  geführt. Dieses wird in der zirka 40fachen  Menge 50     0%iger    Essigsäure gelöst und die  Lösung eiskalt mit der berechneten Menge       Natriumnitritlösung    auf einmal versetzt. Das       Azid    scheidet sich sofort als gelbes Pulver  aus.

   Dieses wird in Äther aufgenommen, die  ätherische Lösung mit Alkohol versetzt, der  Äther     abfraktioniert    und die rückständige  alkoholische Lösung zirka 3 Stunden zum  Sieden erhitzt, wobei sich das     Urethan    bil-         det,    das nach     Abdestillieren    des Alkohols  zurückbleibt. Durch Erhitzen mit konzentrier  ter Salzsäure im Rohr wird das     Urethan    in  das Chlorhydrat des     2-Styryl-4-amin        o-6-äthoxy-          chinolins    übergeführt, das mit Ammoniak auf  freie Base verarbeitet wird.

   Die Base schmilzt  bei 212 0 und bildet mit Milchsäure,     Glykol-          säure    und Chinasäure in Wasser leicht lös  liche Salze.



  Process for the preparation of 2-styiyl-4-amino-6-ethy-quinoline. The subject of this invention is a process for the preparation of 2-styryl-4-amino-6-ethoxy-quinoline, characterized in that 2-styryl 4-carbazido-6-ethoxy-quinoline is heated with an alcohol and the ent Standing urethane treated with saponifying agents. The 2-styryl-4-amino-6-äthöxyquinoline has a strong bactericidal effect and is said to be used in therapy in the form of its salts.



  <I> Example </I> 2-Styryl-6-ethoxy-quinoline-4-carboxylic acid ethyl ester is converted into the 4-hydrazide by heating with excess anhydrous hydrazine in alcoholic solution. This is dissolved in about 40 times the amount of 50% acetic acid and the solution is ice-cold mixed with the calculated amount of sodium nitrite solution at once. The azide precipitates immediately as a yellow powder.

   This is absorbed in ether, the ethereal solution is mixed with alcohol, the ether is fractionated and the residual alcoholic solution is heated to boiling for about 3 hours, whereby the urethane is formed which remains after the alcohol has been distilled off. By heating with concentrated hydrochloric acid in the tube, the urethane is converted into the hydrochloride of 2-styryl-4-amine o-6-ethoxyquinoline, which is processed with ammonia on a free base.

   The base melts at 212 ° and forms salts that are easily soluble in water with lactic acid, glycolic acid and quinic acid.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung von 2-Styryl- 4-amino-6-äthoxy-chinolin, dadurch gekenn zeichnet, dass man 2-Styryl-4-carbazido-6- äthoxy-chinolin mit einem Alkohol erhitzt und das entstandene Urethan mit verseifenden Mitteln behandelt. Das 2-Styryl-4-amino-6- äthogy-chinolin schmilzt bei 212 0 und bildet mit Milchsäure, Glykolsäure und Chinasäure in Wasser leicht lösliche Salze. Es Besitz stark bakterizide Wirkung und soll in Form seiner Salze in der Therapie Verwendung finden. PATENT CLAIM: Process for the preparation of 2-styryl-4-amino-6-ethoxy-quinoline, characterized in that 2-styryl-4-carbazido-6-ethoxy-quinoline is heated with an alcohol and the resulting urethane with saponifying agents treated. The 2-styryl-4-amino-6-ethogy-quinoline melts at 212 ° and forms salts which are easily soluble in water with lactic acid, glycolic acid and quinic acid. It has a strong bactericidal effect and is said to be used in therapy in the form of its salts.
CH127650D 1926-09-07 1926-09-07 Process for the preparation of 2-styryl-4-amino-6-ethoxy-quinoline. CH127650A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH127650T 1926-09-07

Publications (1)

Publication Number Publication Date
CH127650A true CH127650A (en) 1928-09-01

Family

ID=4386189

Family Applications (1)

Application Number Title Priority Date Filing Date
CH127650D CH127650A (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) CH127650A (en)

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