CH171365A - Process for the production of a carbazole derivative. - Google Patents

Process for the production of a carbazole derivative.

Info

Publication number
CH171365A
CH171365A CH171365DA CH171365A CH 171365 A CH171365 A CH 171365A CH 171365D A CH171365D A CH 171365DA CH 171365 A CH171365 A CH 171365A
Authority
CH
Switzerland
Prior art keywords
production
carbazole derivative
weight
parts
formula
Prior art date
Application number
Other languages
German (de)
Inventor
Gesellschaft Fuer Chemis Basel
Original Assignee
Chem Ind Basel
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 Chem Ind Basel filed Critical Chem Ind Basel
Publication of CH171365A publication Critical patent/CH171365A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
    • C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position
    • C09B5/26—Carbazoles of the anthracene series
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/88—Carbazoles; Hydrogenated carbazoles 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Indole Compounds (AREA)

Description

  

  Verfahren zur Herstellung eines     Karbazolderivates.       Es wurde gefunden, dass ein     Karbazol-          derivat    erhalten werden kann, wenn man die  Verbindung der Formel  
EMI0001.0004     
    mit dianotierenden Mitteln behandelt und  das entstandene Produkt hierauf auf höhere  Temperatur erhitzt.  



  Das     Karbazolderivat    der Formel  
EMI0001.0006     
    stellt ein wertvolles Zwischenprodukt zur  Herstellung von Farbstoffen dar. Es bildet  orange gefärbte' Kristalle, die sich in kon  zentrierter Schwefelsäure mit blauer Farbe  lösen und die in organischen Lösungsmitteln  schwer löslich sind.  



  Das     Karbazolderivat    wird besonders glatt  erhalten, wenn das Erhitzen auf höhere Tem  peratur in Gegenwart eines organischen  Lösungsmittels, wie zum Beispiel Nitrobenzol  oder Chlornaphthalin, sowie in Gegenwart  einer organischen Base, wie. zum Beispiel       Dimethylanilin,        Diäthylanilin    oder     Diphenyl-          amin    erfolgt.  



       Beispiel:     120 Gewichtsteile     o'-Nitranilinoarithra-          chinon,    das man zum Beispiel durch Um  setzung von     1-Aminoarithrachinon    mit     o-Nitro-          chlorbenzol    nach     Ullmann    und     Fodor    dar  stellen kann (siehe A. 380, 327), werden 'mit  wenig Sprit     angeteigt,    hierauf mit 2000 Ge-           wichtsteile    Wasser von etwa 60 o versetzt.  Unter Rühren gibt man nun 800 Gewichts  teile 30     %ige    Natronlauge zu und streut so  dann 360 Gewichtsteile     Natriumhydrosulfit     ein.

   Man hält     1/2    Stunde bei<B>50</B> bis 60 o und  oxydiert hierauf mit Luft. Die so dargestellte       o'-Aminoanilinoverbindung    wird nun mit  2000 Gewichtsteilen Wasser angerührt, mit  100 Gewichtsteilen konzentrierter technischer  Salzsäure versetzt und einige Zeit verrührt,  dann wird mit Eis gekühlt und eine Natrium  nitritlösung entsprechend einem Gehalt von  30 Gewichtsteilen     Natriumnitrit    langsam  zugegeben. Man erhitzt hierauf zum Sieden  und filtriert. 50 Gewichtsteile der so erhal  tenen     Aziminoverbindung    werden nun mit  250 Gewichtsteilen Nitrobenzol und 50 Ge  wichtsteilen     Diäthylanilin    solange zum Sieden  erhitzt, bis das Ausgangsmaterial verschwun  den ist.

   Beim Abkühlen kristallisiert das       1.2-Phthaloylkarbazol    aus.



  Process for the production of a carbazole derivative. It has been found that a carbazole derivative can be obtained when using the compound of the formula
EMI0001.0004
    treated with dianotizing agents and the resulting product then heated to a higher temperature.



  The carbazole derivative of the formula
EMI0001.0006
    is a valuable intermediate product for the production of dyes. It forms orange colored crystals which dissolve in concentrated sulfuric acid with a blue color and which are sparingly soluble in organic solvents.



  The carbazole derivative is obtained particularly smoothly when the heating to higher Tem temperature in the presence of an organic solvent such as nitrobenzene or chloronaphthalene, as well as in the presence of an organic base such as. for example dimethylaniline, diethylaniline or diphenylamine takes place.



       Example: 120 parts by weight of o'-nitroanilinoarithrachinone, which can be made into a paste with a little fuel, for example by reacting 1-aminoarithraquinone with o-nitrochlorobenzene according to Ullmann and Fodor (see A. 380, 327) , then mixed with 2000 parts by weight of water at about 60 o. 800 parts by weight of 30% sodium hydroxide solution are then added with stirring, and 360 parts by weight of sodium hydrosulfite are then sprinkled in.

   It is held at <B> 50 </B> to 60 o for 1/2 hour and then oxidized with air. The o'-aminoanilino compound thus prepared is now mixed with 2000 parts by weight of water, 100 parts by weight of concentrated technical hydrochloric acid are added and the mixture is stirred for some time, then it is cooled with ice and a sodium nitrite solution corresponding to 30 parts by weight of sodium nitrite is slowly added. It is then heated to the boil and filtered. 50 parts by weight of the azimino compound obtained in this way are then heated to boiling with 250 parts by weight of nitrobenzene and 50 parts by weight of diethylaniline until the starting material has disappeared.

   The 1,2-phthaloyl carbazole crystallizes out on cooling.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines Karbazol- derivates, dadurch gekennzeichnet, dass man die Verbindung der Formel EMI0002.0012 mit diazotierenden Mitteln behandelt und das entstandene Produkt hierauf auf höhere Tem peratur erhitzt. Das garbazolderivat der Formel EMI0002.0015 stellt ein wertvolles Zwischenprodukt zur Herstellung von Farbstoffen dar. Es bildet orange gefärbte Kristalle, die sich in kon zentrierter Schwefelsäure mit blauer Farbe lösen und die in organischen Lösungsmitteln schwer löslich sind. PATENT CLAIM: Process for the production of a carbazole derivative, characterized in that the compound of the formula EMI0002.0012 treated with diazotizing agents and the resulting product then heated to a higher temperature. The garbazole derivative of the formula EMI0002.0015 is a valuable intermediate product for the production of dyes. It forms orange-colored crystals which dissolve in concentrated sulfuric acid with a blue color and which are sparingly soluble in organic solvents. UNTERANSPRUCH: Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass das Erhitzen auf höhere Temperatur in Gegenwart eines organischen Lösungsmittels; sowie in Gegenwart einer organischen Base erfolgt. SUBClaim: Method according to claim, characterized in that the heating to a higher temperature in the presence of an organic solvent; as well as in the presence of an organic base.
CH171365D 1933-07-20 1933-07-20 Process for the production of a carbazole derivative. CH171365A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH171365T 1933-07-20

Publications (1)

Publication Number Publication Date
CH171365A true CH171365A (en) 1934-08-31

Family

ID=4423030

Family Applications (1)

Application Number Title Priority Date Filing Date
CH171365D CH171365A (en) 1933-07-20 1933-07-20 Process for the production of a carbazole derivative.

Country Status (1)

Country Link
CH (1) CH171365A (en)

Similar Documents

Publication Publication Date Title
DE696591C (en) Process for the production of dyes
DE1026456B (en) Process for the production of Kuepen dyes
CH171365A (en) Process for the production of a carbazole derivative.
CH175875A (en) Process for the production of a carbazole derivative.
DE552927C (en) Process for the production of asymmetrical indigoid dyes
DE639730C (en) Process for the preparation of anthraquinone dyes
DE808601C (en) Process for the production of leuco-sulfuric acid esters of the anthraquinone and indigo series which can be linked
CH175873A (en) Process for the production of a carbazole derivative.
DE581793C (en) Process for the preparation of anthraquinone naphthacridone derivatives
DE533496C (en) Process for the preparation of new compounds of the anthraquinone series
DE356772C (en) Process for the production of dyes
DE495116C (en) Process for the production of black and gray dyes of the benzanthrone series
DE618002C (en) Process for the production of Kuepen dyes
DE725164C (en) Process for the production of Kuepen dyes
AT109696B (en) Process for the preparation of dyes of the anthraquinone series.
CH255319A (en) Process for the production of a vat dye.
CH243338A (en) Process for the production of a new anthraquinone dye.
CH178956A (en) Process for the production of a new anthraquinone dye.
CH217245A (en) Process for the production of a vat dye.
CH280062A (en) Process for the preparation of a nitro dye.
CH216321A (en) Process for the production of an acidic wool dye.
CH166495A (en) Process for the preparation of a dye intermediate.
CH197586A (en) Process for the production of a vat dye of the anthraquinone acridone series.
CH191748A (en) Process for the preparation of an acidic chromating dye of the anthraquinone series.
CH347919A (en) Process for the preparation of dyes of the anthraquinone series