CH287867A - Process for the preparation of 5-oxy-benz (cd) indoline. - Google Patents

Process for the preparation of 5-oxy-benz (cd) indoline.

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Publication number
CH287867A
CH287867A CH287867DA CH287867A CH 287867 A CH287867 A CH 287867A CH 287867D A CH287867D A CH 287867DA CH 287867 A CH287867 A CH 287867A
Authority
CH
Switzerland
Prior art keywords
indoline
benz
oxy
preparation
absorption spectrum
Prior art date
Application number
Other languages
German (de)
Inventor
Ag Haco Gesellschaft
Original Assignee
Haco Ges 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 Haco Ges Ag filed Critical Haco Ges Ag
Publication of CH287867A publication Critical patent/CH287867A/en

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  • Indole Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

  

  Verfahren zur Herstellung von     5-Oxy-benz(ed)        indolin.       In der Patentschrift Nr. 282383 ist ein  Verfahren zur Herstellung von     5-Metlioxy-          N-acetyl-benz(ed)indolin    beschrieben.  



  Die vorliegende Erfindung bezieht sich auf  ein Verfahren zur Herstellung von     5-Oxy-          benz    (cd)     indolin,    welches dadurch gekennzeich  net ist, dass man ein     5-Alkoxy-N-aeyl-benz-          (ed)indolin    unter Erhitzen     hydrolysiert.    Das  Absorptionsspektrum einer alkoholischen Lö  sung des neuen Stoffes weist bei 335 und bei  405     m,u    Maxima auf.  



  Als hydrolytisch wirkende Reagenzien ha  ben sieh     Halogenwasserstoffsäuren    gut be  währt; man verwendet vorzugsweise Brom  wasserstoffsäure in siedendem Eisessig.  



  Das neue Zwischenprodukt soll für die  Herstellung von Heilmitteln verwendet wer  den.  



  <I>Beispiel:</I>  5 g     5-Methoxy    - N -     acetyl-benz    (cd)     indolin     werden in einer Mischung von 40     em3        48-          prozentiger        Bromwasserstoffsäure    und 40     cm3     Eisessig während 11/2 Stunden unter Rück  fluss gekocht.

   Nach längerem Stehen bei -15   wird das ausgeschiedene     Hydrobromid    vom       5-Oxy-benz(ed)indolin        abfiltriert.    Es bildet    gelbe Kristalle, welche im     zugeschmolzenen     Röhrchen bei 234 bis 235  unter Zersetzung  schmelzen, und kann durch     Umkristallisieren     aus     2n-Bromwasserstoffsäure    gereinigt wer  den. Durch Behandlung mit einer wässerigen  Lösung von Silbersulfat kann daraus das Sul  fat hergestellt werden.  



  Die freie Base kann folgendermassen iso  liert werden: 2 Gewichtsteile     Hydrobromid     werden in 25     Volumteilen        ln-Salzsäure    ge  löst. Bei ungefähr 60  wird mit einer ge  sättigten Lösung von     Natriumacetat    versetzt,  bis keine weitere Fällung mehr entsteht. Nach  Abkühlen auf 0  wird das in Form von hell  gelben Kristallen ausgeschiedene     5-Oxy-benz-          (cd)indolin        abfiltriert.    Das Absorptionsspek  trum einer alkoholischen Lösung weist bei  335 und 405     mu    Maxima auf.



  Process for the preparation of 5-oxy-benz (ed) indoline. Patent specification No. 282383 describes a process for the preparation of 5-metlioxy-N-acetyl-benz (ed) indoline.



  The present invention relates to a process for the preparation of 5-oxybenz (cd) indoline, which is characterized in that a 5-alkoxy-N-aeyl-benz- (ed) indoline is hydrolyzed with heating. The absorption spectrum of an alcoholic solution of the new substance shows maxima at 335 and 405 m u.



  As hydrolytically acting reagents have ben see hydrohalic acids well be; it is preferred to use hydrobromic acid in boiling glacial acetic acid.



  The new intermediate is to be used in the manufacture of medicinal products.



  <I> Example: </I> 5 g of 5-methoxy - N - acetyl-benz (cd) indoline are refluxed in a mixture of 40 em3 of 48 percent hydrobromic acid and 40 cm3 of glacial acetic acid for 11/2 hours.

   After standing for a long time at -15, the precipitated hydrobromide is filtered off from the 5-oxy-benz (ed) indoline. It forms yellow crystals, which melt in the closed tube at 234 to 235 with decomposition, and can be purified by recrystallization from 2N hydrobromic acid. Sul fat can be produced from it by treatment with an aqueous solution of silver sulfate.



  The free base can be isolated as follows: 2 parts by weight of hydrobromide are dissolved in 25 parts by volume of ln hydrochloric acid. At about 60 a saturated solution of sodium acetate is added until no further precipitation occurs. After cooling to 0, the 5-oxy-benz- (cd) indoline which separated out in the form of light yellow crystals is filtered off. The absorption spectrum of an alcoholic solution shows maxima at 335 and 405 mu.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von 5-Oxy- benz(ed)indolin, dadurch gekennzeichnet, dass man ein 5-Alkoxy-N-acyl-benz(ed)indolin un ter Erhitzen hydrolysiert. Das Absorptions spektrum einer alkoholischen Lösung des neuen Stoffes weist bei 335 und bei 405 my Maxima auf. PATENT CLAIM: Process for the production of 5-oxybenz (ed) indoline, characterized in that a 5-alkoxy-N-acyl-benz (ed) indoline is hydrolyzed with heating. The absorption spectrum of an alcoholic solution of the new substance shows maxima at 335 and 405 my.
CH287867D 1950-03-11 1950-03-11 Process for the preparation of 5-oxy-benz (cd) indoline. CH287867A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH287867T 1950-03-11

Publications (1)

Publication Number Publication Date
CH287867A true CH287867A (en) 1952-12-31

Family

ID=4485978

Family Applications (1)

Application Number Title Priority Date Filing Date
CH287867D CH287867A (en) 1950-03-11 1950-03-11 Process for the preparation of 5-oxy-benz (cd) indoline.

Country Status (1)

Country Link
CH (1) CH287867A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE958648C (en) * 1953-07-30 1957-02-21 Sandoz Ag Process for the preparation of 4,5-dihydro-9-carbaethoxy-indolo- (4,3-f, g) -quinoline

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE958648C (en) * 1953-07-30 1957-02-21 Sandoz Ag Process for the preparation of 4,5-dihydro-9-carbaethoxy-indolo- (4,3-f, g) -quinoline

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