CH143704A - Process for the preparation of a carbazole derivative. - Google Patents

Process for the preparation of a carbazole derivative.

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Publication number
CH143704A
CH143704A CH143704DA CH143704A CH 143704 A CH143704 A CH 143704A CH 143704D A CH143704D A CH 143704DA CH 143704 A CH143704 A CH 143704A
Authority
CH
Switzerland
Prior art keywords
amidocarbazole
melting point
crystallizes
needles
alcohol
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 CH143704A publication Critical patent/CH143704A/en

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Description

  

  Verfahren zur Darstellung eines     Karbazolderivates.       Gegenstand vorliegender Erfindung ist  ein Verfahren zur Darstellung eines     Karba-          zolderivates,    dadurch gekennzeichnet,     da.ss     man     2-Nitro-3-amidolkarbazol        diazotiert    und  den erhaltenen     Diazokörper    durch Abspalten  der     Azogruppe    in das     ?-Nitrokarbazol    über  führt.  



  <I>Beispiel:</I>  20 Gewichtsteile     2-Nitro-3-amidokarbazol     vom Schmelzpunkt 233 , erhalten zum Bei  spiel nach Kehrmann,     Helv.    XI, 1213 werden  in siedendem Alkohol gelöst. Dann gibt man  etwa. 30 Gewichtsteile einer 20%igen alkoho  lischen Schwefelsäure zu und kühlt durch  Einstellen in Eiswasser ab.

   Unter fortdauern  der Kühlung tropft man eine Lösung von  7 bis 8     Gewichtsteilen        Natriumnitrit    in 14  Gewichtsteilen Wasser zu und erhält so eine  klare     Diazolösung.    Diese wird am     Rückfluss-          kühler    auf dem Wasserbade solange erwärmt,  bis aller Stickstoff abgespalten ist und eine    Probe nicht mehr     mit    einer     sodaalkalischen     Lösung von     1-Naphtol-4-sulfosäure    kuppelt.  Der Stickstoff spaltet sich sehr leicht ab.

    Nach beendigter     Umsetzung    destilliert man  den grössten Teil des Alkohols und     Acetal-          dehyds    ab und versetzt mit heissem Wasser  bis zur Trübung. Der neue Nitrokörper kri  stallisiert nach dem Erkalten aus. Durch       Umkristallisieren    aus Alkohol erhält man ihn  in langen prismatischen Nadeln von orange  gelber Farbe vom Schmelzpunkt 17d .  



  Durch Reduktion erhält man hieraus das       2-Aminokarbazol,    das aus     Xylol    in weissen,  lanzettförmigen Nadeln vom Schmelzpunkt       238     kristallisiert und     mit    dem von Blank,       Ber.    24, 306 beschriebenen identisch ist.  



  Das     Acethyl-2-aminokarbazol    kristalli  siert aus Alkohol in     langen    Nadeln vom  Schmelzpunkt     2,43    bis     244 ,    das     Formyl-2-          amidokarbazol    schmilzt bei 23,9 bis     2,40 ,    das       Benzoyl-2-amidokarbazol    bei 2'76 bis 277 ,  das     p-Toluolsulfo-2-amidokarbazol    bei 188      bis 189  und das     Phenyl-2-amidokarbazol    bei  204 bis 205 . Das neue Produkt soll als Aus  gangsmaterial für Farbstoffe und Arznei  mittel dienen.



  Process for the preparation of a carbazole derivative. The present invention relates to a process for preparing a carbazole derivative, characterized in that 2-nitro-3-amidolcarbazole is diazotized and the diazo body obtained is converted into? -Nitrocarbazole by splitting off the azo group.



  <I> Example: </I> 20 parts by weight of 2-nitro-3-amidocarbazole with a melting point of 233, obtained for example according to Kehrmann, Helv. XI, 1213, are dissolved in boiling alcohol. Then you give about. 30 parts by weight of a 20% alcoholic sulfuric acid and cools by placing in ice water.

   With continued cooling, a solution of 7 to 8 parts by weight of sodium nitrite in 14 parts by weight of water is added dropwise to give a clear diazo solution. This is heated in the reflux condenser on the water bath until all nitrogen has been split off and a sample no longer couples with a soda-alkaline solution of 1-naphthol-4-sulfonic acid. The nitrogen splits off very easily.

    When the reaction is complete, most of the alcohol and acetaldehyde are distilled off and hot water is added until it becomes cloudy. The new nitro body crystallizes out after cooling. It is obtained by recrystallization from alcohol in long prismatic needles of orange-yellow color with a melting point of 17d.



  The 2-aminocarbazole is obtained therefrom by reduction, which crystallizes from xylene in white, lanceolate needles with a melting point of 238 and which is similar to that of Blank, Ber. 24, 306 described is identical.



  The acetyl-2-aminocarbazole crystallizes from alcohol in long needles with a melting point of 2.43 to 244, the formyl-2-amidocarbazole melts at 23.9 to 2.40, the benzoyl-2-amidocarbazole at 2'76 to 277, the p-toluenesulfo-2-amidocarbazole at 188 to 189 and the phenyl-2-amidocarbazole at 204 to 205. The new product is intended to serve as the starting material for dyes and drugs.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines Karba- zolderivates, dadurch gekennzeichnet, dass man 2-Nitro-3-amidoli:arbazol diazotiert und den erhaltenen Diazokörper durch Abspalten der Azogruppe in das 2-Nitrokarbazol über führt. Das neue Produkt kristallisiert aus Alko hol in langen prismatischen Nadeln von orangegelber Farbe vom Schmelzpunkt 175 ". PATENT CLAIM: Process for the preparation of a carbazole derivative, characterized in that 2-nitro-3-amidoli: arbazole is diazotized and the diazo body obtained is converted into 2-nitrocarbazole by splitting off the azo group. The new product crystallizes from alcohol in long prismatic needles of orange-yellow color with a melting point of 175 ". Durch Reduktion erhält man hieraus das 2-Aminokarbazol, das aus Xylol in weissen, lanzettförmigen Nadeln vom Schmelzpunkt ?38 kristallisiert und mit dem von Blank, Ber. 24, 306 beschriebenen identisch ist. From this reduction, 2-aminocarbazole is obtained, which crystallizes from xylene in white, lanceolate-shaped needles with a melting point of 38 and compared with that of Blank, Ber. 24, 306 described is identical. Das Acethyl-2-aminokarbazol kristalli siert aus Alkohol in langen Nadeln vom Schmelzpunkt 243 bis 244 , das Formyl-2- a.midokarbazol schmilzt bei 239 bis 240 , das Benzoyl-2-amidokarbazol bei 27,6 bis 277 , das p-Toluolsulfo-2-amidokarbazol bei 188 bis 189 und das Phenyl-2-amidokarbazol bei 204 bis 205 . Der neue Körper soll als Ausgangsmate rial für Farbstoffe und Arzneimittel dienen. Acethyl-2-aminocarbazole crystallizes from alcohol in long needles with a melting point of 243 to 244, formyl-2-amidocarbazole melts from 239 to 240, benzoyl-2-amidocarbazole from 27.6 to 277, and p-toluenesulfo -2-amidocarbazole at 188 to 189 and the phenyl-2-amidocarbazole at 204 to 205. The new body is to serve as the starting material for dyes and drugs.
CH143704D 1928-01-02 1928-08-30 Process for the preparation of a carbazole derivative. CH143704A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE143704X 1928-01-02

Publications (1)

Publication Number Publication Date
CH143704A true CH143704A (en) 1930-11-30

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Family Applications (1)

Application Number Title Priority Date Filing Date
CH143704D CH143704A (en) 1928-01-02 1928-08-30 Process for the preparation of a carbazole derivative.

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CH (1) CH143704A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015110263A1 (en) * 2014-01-21 2015-07-30 Ac Immune Sa Carbazole and carboline compounds for use in the diagnosis, treatment, alleviation or prevention of disorders associated with amyloid or amyolid-like proteins

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015110263A1 (en) * 2014-01-21 2015-07-30 Ac Immune Sa Carbazole and carboline compounds for use in the diagnosis, treatment, alleviation or prevention of disorders associated with amyloid or amyolid-like proteins
US10662193B2 (en) 2014-01-21 2020-05-26 Ac Immune Sa Carbazole and carboline compounds for use in the diagnosis, treatment, alleviation or prevention of disorders associated with amyloid or amyloid-like proteins

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