DE442609C - Process for the preparation of carbazole-3-carboxylic acid - Google Patents

Process for the preparation of carbazole-3-carboxylic acid

Info

Publication number
DE442609C
DE442609C DEF57068D DEF0057068D DE442609C DE 442609 C DE442609 C DE 442609C DE F57068 D DEF57068 D DE F57068D DE F0057068 D DEF0057068 D DE F0057068D DE 442609 C DE442609 C DE 442609C
Authority
DE
Germany
Prior art keywords
carbazole
carboxylic acid
preparation
acid
carbonic acid
Prior art date
Legal status (The legal status 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 status listed.)
Expired
Application number
DEF57068D
Other languages
German (de)
Inventor
Dr Harry Grimmel
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
IG Farbenindustrie AG
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
Priority to DEF57068D priority Critical patent/DE442609C/en
Application granted granted Critical
Publication of DE442609C publication Critical patent/DE442609C/en
Expired legal-status Critical Current

Links

Classifications

    • 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 des Carbazol-3-carbonsäure. Es ist bekannt, daß beim Erhitzen von Carbazol mit Alkali im Kohlensäurestrom auf 27o° die Carbazol-i-carbonsäure entsteht (vgl. Patentschrift 2q.1 899). Letztere bildet sich aus der primär bei 26o bis 265° entstehenden Carbazol-9-carbonsäure durch Umlagerung zu etwa 7o bis 8o Prozent. Es ist weiter aus der Patentschrift 263 i So bekannt, daß bei erhöhtem Kohlensäuredruck aus den gleichen Komponenten eine Carbazoldicarbons .- tire entsteht.Process for the preparation of carbazole-3-carboxylic acid. It is known, that when carbazole is heated with alkali in a carbonic acid stream to 27o ° the carbazole-i-carboxylic acid arises (see patent specification 2q.1 899). The latter is formed from the primary at 26o to 265 ° resulting carbazole-9-carboxylic acid by rearrangement to about 7o to 8o percent. It is also known from the patent specification 263 i So that with increased Carbonic acid pressure from the same components a Carbazoldicarbons .- tire is created.

Es wurde nun gefunden, daß beim Überleiten von Kohlensäure bei gewöhnlichem Druck über eine Schmelze von Carbazol und Alkali bei Temperaturen über 270° bis 2900 eine zweite Monocarbonsäure entsteht, die allem Anschein nach mit der Carbaz01-3-carhonsäure identisch ist. Ihre Bildung erfolgt analog der Bildung des 3-N itrosocarbazols aus dem 9-I\Titrosocarbazol durch Umlagerung in die beim Carbazol bevorzugte 3-Stellung. Bei Temperatursteigerung über 300° findet Eintritt einer zweiten Carboxylgruppe statt. Die auf diesem Wege erhaltene Carbazol-3-carbonsäure war bisher nur nach der Methode von B o r s c h e und F e i s e (Ber. 40, S. 381 (1907 1) zugänglich. Dieser Weg kommt für die technische Gewinnung nicht in Betracht, während auf dem neuen Wege sich die Säure in sehr guter Ausbeute und beliebiger Menge billig herstellen läßt. Die Säure soll als Ausgangs- und Zwischenprodukt für Farbstoffe Verwendung finden. Beispiel.It has now been found that when passing over carbonic acid with ordinary Pressure over a melt of carbazole and alkali at temperatures above 270 ° to 2900 a second monocarboxylic acid is formed, apparently with Carbaz01-3-carboxylic acid is identical. They are formed analogously to the formation of 3-nitrosocarbazole from the 9-I \ titrosocarbazole by rearrangement into the 3-position preferred for carbazole. When the temperature rises above 300 °, a second carboxyl group occurs instead of. The carbazole-3-carboxylic acid obtained in this way was previously only after the method of B o r s c h e and F e i s e (Ber. 40, p. 381 (1907 1) accessible. This route is out of the question for technical extraction while on the new ways to produce the acid cheaply in very good yield and in any quantity leaves. The acid is said to be used as a starting and intermediate product for dyes Find. Example.

Zoo kg Carbazol und 35 kg Ätzkali werden in einem Eisenkessel mit Rührwerk über freier Flamme i Stunde auf 25o° erhitzt. Dann wird trockene Kohlensäure über die Schmelze geleitet, die Temperatur auf 285° oder gegebenenfalls noch höher gesteigert und i Stunde auf dieser Höhe gehalten. Nach Erkalten wird die Schmelze mit Wasser ausgekocht, filtriert, aus dem Filtrat die rohe Carbonsäure gefällt und getrocknet. Durch Extraktion mit Äther oder Eisessig, in welchem die 3-Carbonsäure schwerlöslich ist, wird sie von etwa mit entstandener i-Carbonsäure befreit und so fast rein erhalten. Sie schmilzt bei 32o°, ihr Äthvlester bei 184°.Zoo kg carbazole and 35 kg caustic potash are in an iron kettle with Stirrer heated to 25o ° over a free flame for one hour. Then it becomes dry carbonic acid Passed over the melt, the temperature to 285 ° or possibly even higher increased and held at this level for an hour. After cooling, the melt becomes Boiled with water, filtered, the crude carboxylic acid precipitated from the filtrate and dried. By extraction with ether or glacial acetic acid, in which the 3-carboxylic acid is sparingly soluble, it is freed from any i-carboxylic acid formed and so almost pure. It melts at 32o °, its ethereal ester at 184 °.

Claims (1)

PATENTANSPRUCI3: Verfahren zur Herstellung der Carbazol-3-carbonsäure, dadurch gekennzeichnet, daß man Carbazol mit Alkali und Kohlensäure bei Temperaturen über 27o°, jedoch nicht höher als 300°, behandelt.PATENT CLAIM3: Process for the production of carbazole-3-carboxylic acid, characterized in that one carbazole with alkali and carbonic acid at temperatures over 27o °, but not higher than 300 °.
DEF57068D 1924-10-09 1924-10-09 Process for the preparation of carbazole-3-carboxylic acid Expired DE442609C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEF57068D DE442609C (en) 1924-10-09 1924-10-09 Process for the preparation of carbazole-3-carboxylic acid

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF57068D DE442609C (en) 1924-10-09 1924-10-09 Process for the preparation of carbazole-3-carboxylic acid

Publications (1)

Publication Number Publication Date
DE442609C true DE442609C (en) 1927-04-04

Family

ID=7108160

Family Applications (1)

Application Number Title Priority Date Filing Date
DEF57068D Expired DE442609C (en) 1924-10-09 1924-10-09 Process for the preparation of carbazole-3-carboxylic acid

Country Status (1)

Country Link
DE (1) DE442609C (en)

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