CH253474A - Process for the preparation of 5-chloro-8-oxy-quinaldine. - Google Patents

Process for the preparation of 5-chloro-8-oxy-quinaldine.

Info

Publication number
CH253474A
CH253474A CH253474DA CH253474A CH 253474 A CH253474 A CH 253474A CH 253474D A CH253474D A CH 253474DA CH 253474 A CH253474 A CH 253474A
Authority
CH
Switzerland
Prior art keywords
chloro
quinaldine
oxy
preparation
acid
Prior art date
Application number
Other languages
German (de)
Inventor
Elisabeth Dr Pfanner
Original Assignee
Elisabeth Dr Pfanner
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 Elisabeth Dr Pfanner filed Critical Elisabeth Dr Pfanner
Publication of CH253474A publication Critical patent/CH253474A/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
    • C07D215/20—Oxygen atoms
    • C07D215/24—Oxygen atoms attached in position 8
    • C07D215/26—Alcohols; Ethers thereof
    • C07D215/28—Alcohols; Ethers thereof with halogen atoms or nitro radicals in positions 5, 6 or 7

Description

  

  Verfahren zur Herstellung von     5-Chlor-8-oxy-chinaldin.       Es hat sich gezeigt, dass man das be  kannte, als Desinfektionsmittel     verwendbare          5-Chlor-8-oxy-chinaldin    direkt aus     4-Chlor-          2-amino-phenol    erhalten kann, ohne dass man  zuerst das     8-Oxy-chinaldin        herstellt    und die  ses nachträglich chloriert. Nach dem neuen  Verfahren     lä,sst    man     Crotonaldehyd    in An  wesenheit von Säure auf     4-Chlor-2-amino-          pbenol    einwirken.

   Nachdem die     Selbsterwär-          mung    aufgehört hat, kann das Reaktions  gemisch noch einige Zeit     stehengelas,sen    oder  einige Zeit unter     Rückfluss    zum Sieden er  hitzt werden. Durch Neutralisation und Fil  tration oder durch Neutralisation und an  sehliessende     Wasserdampfdestillation    kann  das     5-Chlor-8-ogy-chinaldin        isoliert    werden.  



  Zur Kondensation eignet .sich am besten       Crotonaadehyd,    doch kann dieser auch zum  Beispiel, wenn auch     weniger    zweckmässig,  durch     Acetaldehyd,        Paraldehyd,        Acetal    oder       Aldol    ersetzt werden, die alle     intermediär          Crotonaldehyd    bilden. Als Säure kann man       ,Salzsäure    oder zum Beispiel     Bromwasser-          stoffsä.ure,    Schwefelsäure oder Phosphor  säure verwenden.

   Auch kann man durch Zu  uatz von Metallsalzen, wie Zinkchlorid,     Zinn-          ehlorid    oder Aluminiumchlorid, oder auch       ,Metallen    selbst die Reaktion     beschleunigen     und die     Ausbeute    verbessern.         Beispiel:     50g     4-Chlor-2-amino-phenol,        80g    kon  zentrierte Salzsäure und 70 g     Paraldehyd          %verden    mit einem Zusatz von Aluminium  chlorid in einem Kolben     zusammengebracht.     Dabei erwärmt sich die Lösung .sehr stark  von selbst.

   Man lässt nun     eine    Zeitlang ste  hen, zweckmässig bis zu 10     Stunden.    An  schliessend erhitzt man noch 2 Stunden unter       Rückfluss    zum     Sieden.    Das Reaktionsprodukt  wird nun, um das     5-Chlor-8-oxy-chinaldin    zu  fällen, ohne     vorgängiges        Filtrieren        neutrali-          siert    und     wasserdampfdesstilliert,    wobei das  Produkt direkt kristallin ausfällt. Schmelz  punkt     84 .  



  Process for the preparation of 5-chloro-8-oxy-quinaldine. It has been shown that the known 5-chloro-8-oxy-quinaldine which can be used as a disinfectant can be obtained directly from 4-chloro-2-aminophenol without first producing the 8-oxy-quinaldine and the ses subsequently chlorinated. According to the new process, crotonaldehyde is allowed to act on 4-chloro-2-aminopbenol in the presence of acid.

   After the self-heating has ceased, the reaction mixture can be left to stand for some time or heated to boiling under reflux for some time. The 5-chloro-8-ogy-quinaldine can be isolated by neutralization and Fil tration or by neutralization and subsequent steam distillation.



  Crotonaldehyde is best suited for condensation, but it can also be replaced, for example, if less expediently, by acetaldehyde, paraldehyde, acetal or aldol, all of which form crotonaldehyde as an intermediate. The acid used can be hydrochloric acid or, for example, hydrobromic acid, sulfuric acid or phosphoric acid.

   It is also possible to accelerate the reaction and improve the yield by adding metal salts such as zinc chloride, tin chloride or aluminum chloride, or even metals themselves. Example: 50 g of 4-chloro-2-aminophenol, 80 g of concentrated hydrochloric acid and 70 g of paraldehyde% are combined in a flask with an addition of aluminum chloride. The solution heats up very strongly by itself.

   You can now stand for a while, expediently up to 10 hours. The mixture is then heated to boiling under reflux for a further 2 hours. In order to precipitate the 5-chloro-8-oxy-quinaldine, the reaction product is then neutralized without prior filtering and steam-distilled, the product precipitating directly in crystalline form. Melting point 84.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von 5-Chlor- 8.-oxy-chinaldin, dadurch gekennzeichnet, dass man Crotonaldellyd in Anwesenheit von Säure auf 4-Chlor-2-amino-phenol einwirken lässt. <B>UNTERANSPRÜCHE:</B> 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, da.ss man in Gegen wart eines Metallkatalysators arbeitet. 2. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man in Gegenwart eines Metallsalzkatalysators arbeitet. PATENT CLAIM: Process for the production of 5-chloro-8.-oxy-quinaldine, characterized in that crotonaldellyd is allowed to act on 4-chloro-2-aminophenol in the presence of acid. <B> SUBClaims: </B> 1. Method according to claim, characterized in that one works in the presence of a metal catalyst. 2. The method according to claim, characterized in that one works in the presence of a metal salt catalyst.
CH253474D 1943-12-31 1943-12-31 Process for the preparation of 5-chloro-8-oxy-quinaldine. CH253474A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH253474T 1943-12-31

Publications (1)

Publication Number Publication Date
CH253474A true CH253474A (en) 1948-03-15

Family

ID=4470013

Family Applications (1)

Application Number Title Priority Date Filing Date
CH253474D CH253474A (en) 1943-12-31 1943-12-31 Process for the preparation of 5-chloro-8-oxy-quinaldine.

Country Status (1)

Country Link
CH (1) CH253474A (en)

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