CH124931A - Process for the preparation of 6-methoxy-N- (a-dimethylamino-a-methyl-propyl) -8-aminoquinoline. - Google Patents

Process for the preparation of 6-methoxy-N- (a-dimethylamino-a-methyl-propyl) -8-aminoquinoline.

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Publication number
CH124931A
CH124931A CH124931DA CH124931A CH 124931 A CH124931 A CH 124931A CH 124931D A CH124931D A CH 124931DA CH 124931 A CH124931 A CH 124931A
Authority
CH
Switzerland
Prior art keywords
aminoquinoline
dimethylamino
methoxy
propyl
methyl
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 CH124931A publication Critical patent/CH124931A/en

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Description

  

  Verfahren zur Darstellung von     6-Nethogy-N-(a-Dimethylamino-a-methyl-propyl)-          8-aminoehinolin.       Gegenstand vorliegender Erfindung ist  ein Verfahren zur Darstellung von 6-Me       thoxy-N-(a-Dimethylamino-a-methyl-propyl)-          8-aminochinolin.    Dieses Verfahren ist da  durch gekennzeichnet,

       daB    man     6-Methoxy-          8-aminochinolin    mit einem in     y-Stellung     durch einen reaktionsfähigen     Substituenten     substituierten     a-Dimethylamino    - a -     methyl-          propan    zur     Umsetzung    bringt.  



  Die neue Verbindung bildet ein gelbes 01  mit dem Siedepunkt 180 bis 184   C bei  1,5 mm Druck. Sie bildet ein festes, in Was  ser leicht lösliches, orangefarbenes Chlor  hydrat und soll als therapeutisch ausseror  dentlich wertvolles, spezifisch wirksames  Heilmittel     Verwendung    finden.  



       Beispiel:     Zur Darstellung von     6-Methoxy-N-(a-          dimethylamino    - a -     methyl    -     propyl)    -8-     amino-          chinolin     
EMI0001.0022     
    werden 172 Gewichtsteile Chlorhydrat des       a-Dimethylamino-a-methyl    -     propylchlorids     mit 174 Gewichtsteilen     6-Methoxy-8-amino-          chinolin    bei 120 bis<B>130'</B> während 8 Stun  den verschmolzen. Die Schmelze wird in  Wasser gelöst, alkalisch gemacht und die  ausgeschiedene Base in Äther aufgenommen.

    Die neue Verbindung destilliert als gelbes  <B>01</B> bei 180 bis 1.84' bei 1,5 mm Druck. Sie  bildet ein festes, in Wasser leicht lösliches,  orangefarbenes Chlorhydrat. Die Darstel  lung dieser Verbindung kann auch erfolgen,  indem man die beiden Komponenten bei Ge  genwart eines Lösungsmittels, verdünnter  Alkohol oder Wasser, auf Kochtemperatur  erhitzt. Ebenso kann auch an Stelle des       Chlorides    der entsprechende     p-Toluolsulfo-          säureester    zur Anwendung gelangen.



  Process for the preparation of 6-Nethogy-N- (a-Dimethylamino-a-methyl-propyl) - 8-aminoehinoline. The present invention relates to a process for the preparation of 6-methoxy-N- (a-dimethylamino-a-methyl-propyl) - 8-aminoquinoline. This procedure is characterized by

       that 6-methoxy-8-aminoquinoline is reacted with an a-dimethylamino-a-methylpropane substituted in the y-position by a reactive substituent.



  The new compound forms a yellow oil with a boiling point of 180 to 184 C at 1.5 mm pressure. It forms a solid, orange-colored chlorine hydrate that is easily soluble in water and is said to be used as a therapeutically extremely valuable, specifically effective remedy.



       Example: For the preparation of 6-methoxy-N- (a-dimethylamino-a-methyl-propyl) -8-amino-quinoline
EMI0001.0022
    172 parts by weight of a-dimethylamino-a-methyl-propyl chloride are fused with 174 parts by weight of 6-methoxy-8-aminoquinoline at 120 to 130 'for 8 hours. The melt is dissolved in water, made alkaline and the precipitated base is taken up in ether.

    The new compound distills as a yellow <B> 01 </B> at 180 to 1.84 'at 1.5 mm pressure. It forms a solid, orange-colored hydrochloride that is easily soluble in water. This compound can also be represented by heating the two components to boiling temperature in the presence of a solvent, dilute alcohol or water. The corresponding p-toluenesulfonic acid ester can also be used instead of the chloride.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung von 6-Me thoxy-N-(a-Dimethylamino-a-methyl-propyl)- 8-aminochinolin, dadurch gekennzeichnet, daB man 6-lllethoxy-8-aminochinolin mit einem in y-Stellung durch einen reaktions- fähigen Substituenten substituierten a-Dinie- tliy lamino-a-metliylpropa.n zur Umsetzung bringt. Die neue Verbindung bildet ein gelbes C)1 mit dem Siedepunkt 180 bis 184 C bei 1,5 mm Druck. PATENT CLAIM: Process for the preparation of 6-methoxy-N- (a-dimethylamino-a-methyl-propyl) -8-aminoquinoline, characterized in that 6-III-ethoxy-8-aminoquinoline is reacted with one in the y-position - Capable substituents substituted a-Dinietliy lamino-a-metliylpropa.n brings to implementation. The new compound forms a yellow C) 1 with a boiling point of 180 to 184 C at 1.5 mm pressure. Sie bildet ein festes, in Was- ser leicht lösliches, orangefarbenes Chlor hydrat und soll als therapeutisch ausseror dentlich wertvolles, spezifisch wirksames Heilmittel Verwendung finden. UNTERANSPRUCH: Verfahren nach Patentanspruch. da durch ,ehcnnzeichnet, da.ss man die Um setzung in Gegenwart eines Lösungsmittels vornimmt. It forms a solid, orange-colored chlorine hydrate that is easily soluble in water and is said to be used as a therapeutically extremely valuable, specifically effective remedy. SUBClaim: Method according to patent claim. This is because the reaction is carried out in the presence of a solvent.
CH124931D 1924-09-11 1925-08-08 Process for the preparation of 6-methoxy-N- (a-dimethylamino-a-methyl-propyl) -8-aminoquinoline. CH124931A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE124931X 1924-09-11
CH123059T 1925-08-08

Publications (1)

Publication Number Publication Date
CH124931A true CH124931A (en) 1928-03-16

Family

ID=25710002

Family Applications (1)

Application Number Title Priority Date Filing Date
CH124931D CH124931A (en) 1924-09-11 1925-08-08 Process for the preparation of 6-methoxy-N- (a-dimethylamino-a-methyl-propyl) -8-aminoquinoline.

Country Status (1)

Country Link
CH (1) CH124931A (en)

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