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CH170617A - Process for obtaining a therapeutically valuable compound of the heterocyclic series. - Google Patents

Process for obtaining a therapeutically valuable compound of the heterocyclic series.

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Publication number
CH170617A
CH170617A CH170617DA CH170617A CH 170617 A CH170617 A CH 170617A CH 170617D A CH170617D A CH 170617DA CH 170617 A CH170617 A CH 170617A
Authority
CH
Switzerland
Prior art keywords
obtaining
therapeutically valuable
heterocyclic series
valuable compound
solution
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 CH170617A publication Critical patent/CH170617A/en

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Description

  

  Verfahren zur Gewinnung einer therapeutisch     wertvollen    Verbindung  der     heterocyclischen    Reihe.    Gegenstand des vorliegenden Patentes  ist ein Verfahren zur Darstellung einer     qua-          ternären    Verbindung des N,     N'-Di-ohinolyl-6-          harnstoffes.    Dieses Verfahren ist dadurch ge  kennzeichnet,     dassmanaufeineN-Methylchino-          linium-6-car-bonsäurehydrazid-jon    enthaltende  wässerige salzsaure Lösung     Natriumnitrit    ein  wirken lässt, die Mineralsäure abstumpft und  die Lösung kocht.

   Der so erhältliche symmetri  sche     Harnstoff    des     6-Amino-N-methylchinoli-          niumchlorids    ist ein in Wasser lösliches Salz und  schmilzt bei<B>260'</B> unter Zersetzung. Er soll  therapeutische Anwendung finden.  



  <I>Beispiel:</I>  Eine Lösung, die 10     gr    eines Salzes des       N-Methylchinoliir-6-earbonsäurehydrazids    ent  hält (beispielsweise darstellbar aus     Chinolin-          6-carbonsäurehydrazid    durch Anlagerung von       Di-methylsulfat),    wird mit verdünnter Salz  säure eben angesäuert, auf 0   abgekühlt und  mit     Natriumnitritlösung    versetzt, bis eben    freie, salpetrige Säure nachweisbar ist. Danach  wird die überschüssige Salzsäure mit Natrium  acetatlösung abgestumpft und die so erhal  tene Lösung zum Sieden erhitzt, bis die Gas  entwicklung beendet ist.

   Nach dem Erkalten  wird mit verdünnter Salzsäure eben kongo  sauer gestellt, die Lösung im Vakuum bei  20-2b   eingedampft und der erhaltene Salz  rückstand mit Methylalkohol extrahiert. Nach  Einengen der     methylalkoholischen    Lösung  erhält man durch Zugabe von alkoholischer  Salzsäure den symmetrischen     Harnstoff    des       6-Amino-N-methylchinoliniuinchlorids    als ein  in Wasser lösliches Salz, das bei<B>260'</B> unter       Zersetzunz    schmilzt.



  Process for obtaining a therapeutically valuable compound of the heterocyclic series. The subject matter of the present patent is a process for the preparation of a quaternary compound of N, N'-di-ohinolyl-6-urea. This process is characterized in that sodium nitrite is allowed to act on an aqueous hydrochloric acid solution containing N-methylquinoline-6-carboxylic acid hydrazide ion, the mineral acid is blunted and the solution is boiled.

   The symmetrical urea of 6-amino-N-methylquinolinium chloride obtainable in this way is a salt soluble in water and melts at <B> 260 '</B> with decomposition. It should find therapeutic application.



  <I> Example: </I> A solution that contains 10 grams of a salt of N-methylquinoline-6-carboxylic acid hydrazide (for example, can be prepared from quinoline-6-carboxylic acid hydrazide by the addition of dimethyl sulfate) becomes even with dilute hydrochloric acid acidified, cooled to 0 and mixed with sodium nitrite solution until free, nitrous acid can be detected. Thereafter, the excess hydrochloric acid is truncated with sodium acetate solution and the resulting solution is heated to boiling until the evolution of gas has ended.

   After cooling, the Congo is acidified with dilute hydrochloric acid, the solution is evaporated in vacuo at 20-2b and the salt residue obtained is extracted with methyl alcohol. After the methyl alcoholic solution has been concentrated, the symmetrical urea of the 6-amino-N-methylquinoline chloride is obtained as a water-soluble salt which melts at <B> 260 '</B> with decomposition by adding alcoholic hydrochloric acid.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung einer quater- nären Verbindung des N, N'-Di-chinolyl-6- harnstoffes, dadurch gekennzeichnet, dass man auf eine N-Methylchinolinium-6-carbonsäure- hydrazid-jon enthaltende wässerige salzsaure Lösung Natriumnitrit einwirken lässt, die Mineralsäure abstumpft und die Lösung kocht. Der so erhältliche symmetrische Harnstoff des 6-Amino-N-methylchinoliniumchlorids ist ein in Wasser lösliches Salz und schmilzt bei 260d unter Zersetzung. PATENT CLAIM: Process for the preparation of a quaternary compound of N, N'-di-quinolyl-6-urea, characterized in that sodium nitrite is allowed to act on an aqueous hydrochloric acid solution containing N-methylquinolinium-6-carboxylic acid hydrazide-ion, the mineral acid dulls and the solution boils. The symmetrical urea of 6-amino-N-methylquinolinium chloride which can be obtained in this way is a salt which is soluble in water and melts at 260d with decomposition. Er soll thera peutische Anwendung finden. It should find therapeutic application.
CH170617D 1931-08-18 1932-08-17 Process for obtaining a therapeutically valuable compound of the heterocyclic series. CH170617A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE170617X 1931-08-18

Publications (1)

Publication Number Publication Date
CH170617A true CH170617A (en) 1934-07-15

Family

ID=5688849

Family Applications (1)

Application Number Title Priority Date Filing Date
CH170617D CH170617A (en) 1931-08-18 1932-08-17 Process for obtaining a therapeutically valuable compound of the heterocyclic series.

Country Status (1)

Country Link
CH (1) CH170617A (en)

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