CH212595A - Process for the preparation of a quinoline compound containing a basic substituted amino group in the 4-position. - Google Patents

Process for the preparation of a quinoline compound containing a basic substituted amino group in the 4-position.

Info

Publication number
CH212595A
CH212595A CH212595DA CH212595A CH 212595 A CH212595 A CH 212595A CH 212595D A CH212595D A CH 212595DA CH 212595 A CH212595 A CH 212595A
Authority
CH
Switzerland
Prior art keywords
preparation
amino group
compound containing
substituted amino
quinoline compound
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 CH212595A publication Critical patent/CH212595A/en

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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
    • C07D215/46—Nitrogen atoms attached in position 4 with hydrocarbon radicals, substituted by nitrogen atoms, attached to said nitrogen atoms

Landscapes

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

Description

  

  Verfahren zur Herstellung einer in     4-Stellung    eine basisch substituierte       Aminogruppe    enthaltenden     Chinolinverbindung.       Das Hauptpatent     betrifft    ein Verfahren  zur Darstellung einer     therapeutisch    wert  vollen     Chinolinverbindung.     



  Gegenstand des vorliegenden Patentes ist  ein Verfahren zur Herstellung einer in     4-          Stellung    eine basisch substituierte     Amino-          gruppe    enthaltenden Verbindung. Das Ver  fahren ist dadurch gekennzeichnet, dass man  4.     7-Dichlor-3-methylchinolin    mit     1-Diäthyl-          amino-4-aminobutan    zum     3-Methyl-4-diäthyl-          aminobutylamino-7-chlorchinolin    umsetzt. Die  Umsetzung erfolgt zum Beispiel durch Er  wärmen der genannten Ausgangsstoffe auf  höhere Temperaturen, z.

   B. auf etwa 170 bis  <B>180',</B> in Gegenwart von     Jodnatrium.    Die  Aufarbeitung dieser     Reaktionsmischung    er  folgt zum Beispiel in üblicher Weise. Der  Schmelzpunkt des Reaktionsproduktes in  Form seines Hydrochlorids liegt bei 195  .    <I>Beispiel:</I>  21,2 g 4.     7-Dichlor-3-methylcbinolin    wer  den mit 21g Phenol, 30 g     1-Diäthylamino-4-          aminobutan    und 0,1 g     Jodnatrium    15 Stun  den auf 170 bis<B>180'</B> erhitzt. Die Schmelze  wird mit überschüssiger 32%iger Natron  lauge versetzt und wiederholt mit Äther ex  trahiert. Der Ätherlösung werden die Basen  durch Ausschütteln mit verdünnter Salzsäure  entzogen.

   Die salzsaure Lösung wird durch  Zugabe von Natronlauge stark alkalisch ge  macht und     ausgeäthert.    Nach Verdampfen  des Äthers wird     fraktioniert    destilliert. Die  Fraktion vom Siedepunkt 217 bis 226   bei  1,5 mm Druck wird     in    wenig Alkohol gelöst  und mit alkoholischer     Chlorwasserstoffsäure     bis zur kongosauren Reaktion versetzt. Dann  gibt man bis zur Trübung Essigester hinzu  und lässt kristallisieren. Die ausgeschiedenen  farblosen Kristalle stellen das Hydrochlorid      des     3-Methyl-4-diäthylaminobutylamino-7-          chlorchinolins    dar. Ihr Schmelzpunkt liegt  bei 195  .



  Process for the preparation of a quinoline compound containing a basic substituted amino group in position 4. The main patent relates to a method for preparing a therapeutically valuable quinoline compound.



  The subject of the present patent is a process for the preparation of a compound containing a basic substituted amino group in the 4-position. The process is characterized in that 4. 7-dichloro-3-methylquinoline is reacted with 1-diethylamino-4-aminobutane to give 3-methyl-4-diethylaminobutylamino-7-chloroquinoline. The implementation takes place, for example, by He warming the starting materials mentioned to higher temperatures, eg.

   B. to about 170 to <B> 180 ', </B> in the presence of sodium iodine. This reaction mixture is worked up, for example, in the customary manner. The melting point of the reaction product in the form of its hydrochloride is 195. <I> Example: </I> 21.2 g of 4. 7-dichloro-3-methylcbinoline are treated with 21 g of phenol, 30 g of 1-diethylamino-4-aminobutane and 0.1 g of sodium iodine for 15 hours to 170 to < B> 180 '</B> heated. The melt is mixed with excess 32% sodium hydroxide solution and repeatedly extracted with ether. The bases are removed from the ethereal solution by shaking out with dilute hydrochloric acid.

   The hydrochloric acid solution is made strongly alkaline by adding sodium hydroxide solution and then etherified. After evaporation of the ether, fractional distillation is carried out. The fraction from boiling point 217 to 226 at 1.5 mm pressure is dissolved in a little alcohol and mixed with alcoholic hydrochloric acid until the Congo acidic reaction occurs. Then ethyl acetate is added until cloudy and allowed to crystallize. The precipitated colorless crystals represent the hydrochloride of 3-methyl-4-diethylaminobutylamino-7-chloroquinoline. Their melting point is 195.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung einer in 4- Stellung eine basisch substituierte Amino- gruppe enthaltenden Chinolinverbindung, da durch gekennzeichnet, dass man 4. 7-Diehlor- 3 - methyl - chinolin mit 1. - Diäthylamino - 4 - aminobutan zum 3-3Tethyl-4-diäthylamino- butylamino-7-chlorcliinolin umsetzt. PATENT CLAIM: Process for the preparation of a quinoline compound containing a basic substituted amino group in the 4-position, characterized in that 4. 7-Diehlor- 3 - methyl - quinoline with 1. - diethylamino - 4 - aminobutane to 3-3Tethyl- 4-diethylamino-butylamino-7-chloroclinoline is implemented. Das so erhaltene neue Produkt zeigt in Form des IIVClroclilorlds einen Schmelzpunkt von 195 . The new product obtained in this way has a melting point of 195 in the form of IIV Clroclilorld.
CH212595D 1937-10-07 1938-09-15 Process for the preparation of a quinoline compound containing a basic substituted amino group in the 4-position. CH212595A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE212595X 1937-10-07
CH209465T 1938-09-15

Publications (1)

Publication Number Publication Date
CH212595A true CH212595A (en) 1940-11-30

Family

ID=25724731

Family Applications (1)

Application Number Title Priority Date Filing Date
CH212595D CH212595A (en) 1937-10-07 1938-09-15 Process for the preparation of a quinoline compound containing a basic substituted amino group in the 4-position.

Country Status (1)

Country Link
CH (1) CH212595A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2758997A (en) * 1953-03-19 1956-08-14 Sterling Drug Inc 7-chloro-4-(4-di-n-butylaminobutylamino)-3-methylquinoline and salts thereof

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2758997A (en) * 1953-03-19 1956-08-14 Sterling Drug Inc 7-chloro-4-(4-di-n-butylaminobutylamino)-3-methylquinoline and salts thereof

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