CH94982A - Process for the preparation of an acridine derivative. - Google Patents

Process for the preparation of an acridine derivative.

Info

Publication number
CH94982A
CH94982A CH94982DA CH94982A CH 94982 A CH94982 A CH 94982A CH 94982D A CH94982D A CH 94982DA CH 94982 A CH94982 A CH 94982A
Authority
CH
Switzerland
Prior art keywords
acridine
parts
preparation
ethoxy
acridine derivative
Prior art date
Application number
Other languages
German (de)
Inventor
Farbwerke Vorm Meiste Bruening
Original Assignee
Hoechst 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 Hoechst Ag filed Critical Hoechst Ag
Publication of CH94982A publication Critical patent/CH94982A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
    • C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems 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 carbon atoms of the ring system
    • C07D219/08—Nitrogen atoms
    • C07D219/10—Nitrogen atoms attached in position 9

Description

  

      Verfahren    zur Darstellung eines     Aeridinderivates.       In dem Zusatzpatent Nr. 93753 würde  ein Verfahren zur Darstellung von 3.9.7  1)iamino-äthoxy-acridin beschrieben, darin  bestehend, dass man das aus     3.9.7-Nitro-          lialogen-ä        thoxy-acriclin    erhältliche 3 . 9 .     7-          Nitro-amino-äthoxy-acridin    reduziert.

   Es       wurde    nun gefunden, dass man dieselbe Ver  bindung auch erhält, wenn man ein 3.9     .7-          :lniino-liydrazino-äthoxy-acridin,    aus dem  . 9 . 7:     Amino@halogen-äthoxy-,ae@ridin    (siehe  Patent Nr. 93752) durch Umsetzung mit  einem     ITydrazin,    zum Beispiel mit     Phenyl-          hydrazin,    entstehend, reduziert.  



  <I>Beispiel</I>  35 Teile 3 . 9 .     7-Amino-chlor-äthoxy-acri-          din    werden mit 200 Teilen     Amylalkohol    und:  15 Teilen     Phenylhydrazin    versetzt und unter  Rühren etwa eine Stunde auf 80   erwärmt.       Es    entsteht zuerst eine Lösung, aus der sich  dann das salzsaure     3.9.7-Amino-phenyl-          hyclrazino-iLthoxy-acridin    ausscheidet. 30  Teile dieser Verbindung werden in 50 Tei  len 50     %iger    Essigsäure suspendiert und auf  <B>80 '</B> erwärmt. Dann trägt man allmählich  12 Teile     Zinkstaub    ein.

   Nach mehrstündigem  Erwärmen ist eine rotbraune Lösung     ent-          slanden,    aus der sich beim Erkalten das salz-    saure 3 . 9 .     7-Diamino-äthoxy-acridin    ab  scheidet. Es wird durch Lösen in Wasser  und Wiederausscheiden durch Zugabe von  konzentrierter Salzsäure gereinigt und bildet  dann ein gelbes Pulver. Das aus diesem Salz  abgeschiedene     3.9.7-Diamiiio-ätlioxy-acridin     schmilzt bei 124'.  



       Beispiel   <I>2</I>  10 Teile des 3 . 9 .     7-Diamino-pheny        1-          hydrazino-äthoxy-a,cridin-Chlorhydrats    -wer  den in 50 Teilen 50     %igem    Alkohol gelöst.  5 Teile Chlorammonium und 5 Teile Zink  staub hinzugegeben .und einige Stunden auf  dem Wasserbad erwärmt. Aus der wässerigen  Lösung wird sodann durch Zugabe von Koch  salzlösung das salzsaure     3.9.7-Diamino-          äthoxy-acridin    gefällt.



      Process for the preparation of an aeridine derivative. In the additional patent no. 93753 a process for the preparation of 3.9.7 1) iamino-ethoxy-acridine would be described, consisting in the fact that the 3. 9. 7-nitro-amino-ethoxy-acridine reduced.

   It has now been found that the same connection is also obtained when a 3.9 .7-: lniino-liydrazino-ethoxy-acridine, from the. 9. 7: Amino @ halogen-ethoxy-, ae @ ridin (see patent no. 93752) resulting from reaction with an ITydrazine, for example with phenylhydrazine, reduced.



  <I> Example </I> 35 parts 3. 9. 7-Amino-chloro-ethoxy-acridine are mixed with 200 parts of amyl alcohol and: 15 parts of phenylhydrazine and heated to 80 for about an hour while stirring. First a solution is formed from which the hydrochloric acid 3.9.7-amino-phenyl-hyclrazino-iLthoxy-acridine is precipitated. 30 parts of this compound are suspended in 50 parts of 50% acetic acid and heated to <B> 80 '</B>. Then gradually 12 parts of zinc dust are introduced.

   After several hours of warming, a red-brown solution has been released from which the hydrochloric acid 3. 9. 7-diamino-ethoxy-acridine separates. It is purified by dissolving it in water and precipitating it again by adding concentrated hydrochloric acid and then forms a yellow powder. The 3.9.7-diamiiio-ätlioxy-acridine separated from this salt melts at 124 '.



       Example <I> 2 </I> 10 parts of the 3rd 9. 7-diamino-pheny 1- hydrazino-ethoxy-a, cridine-chlorohydrates -wer the dissolved in 50 parts of 50% alcohol. 5 parts of chlorammonium and 5 parts of zinc dust were added and heated for a few hours on a water bath. The hydrochloric acid 3.9.7-diaminoethoxy-acridine is then precipitated from the aqueous solution by adding sodium chloride solution.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung von 3.9. 7 Diamino-ä,thoxy-acridin, darin bestehend, dass man ein 3 . 9 . 7-Amino-hydra.zino-ätb oxy- acridin reduziert. PATENT CLAIM: Method for the representation of 3.9. 7 diamino-ä, thoxy-acridine, consisting in the fact that one has a 3. 9. 7-amino-hydra.zino-ätb oxy-acridin reduced.
CH94982D 1921-09-12 1921-09-12 Process for the preparation of an acridine derivative. CH94982A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH93439T 1921-09-12
CH94982T 1921-09-12

Publications (1)

Publication Number Publication Date
CH94982A true CH94982A (en) 1922-10-02

Family

ID=25704666

Family Applications (1)

Application Number Title Priority Date Filing Date
CH94982D CH94982A (en) 1921-09-12 1921-09-12 Process for the preparation of an acridine derivative.

Country Status (1)

Country Link
CH (1) CH94982A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4544659A (en) * 1982-11-26 1985-10-01 Hoffman-La Roche Inc. Schistosomicidal acridanone hydrazones
US4711889A (en) * 1983-11-15 1987-12-08 Hoffman-La Roche Inc. Schistosomicidal acridanone hydrazones

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4544659A (en) * 1982-11-26 1985-10-01 Hoffman-La Roche Inc. Schistosomicidal acridanone hydrazones
US4711889A (en) * 1983-11-15 1987-12-08 Hoffman-La Roche Inc. Schistosomicidal acridanone hydrazones

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