CH143702A - Process for the preparation of a carbazole derivative. - Google Patents
Process for the preparation of a carbazole derivative.Info
- Publication number
- CH143702A CH143702A CH143702DA CH143702A CH 143702 A CH143702 A CH 143702A CH 143702D A CH143702D A CH 143702DA CH 143702 A CH143702 A CH 143702A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- carbazole derivative
- oxycarbazole
- carbazole
- derivative
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 4
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 title claims 2
- 239000000975 dye Substances 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 229940127557 pharmaceutical product Drugs 0.000 claims 1
- 239000002994 raw material Substances 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000001716 carbazoles Chemical class 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- YJKJAYFKPIUBAW-UHFFFAOYSA-N 9h-carbazol-1-amine Chemical class N1C2=CC=CC=C2C2=C1C(N)=CC=C2 YJKJAYFKPIUBAW-UHFFFAOYSA-N 0.000 description 1
- DHHFGQADZVYGIE-UHFFFAOYSA-N 9h-carbazole-1-carboxylic acid Chemical class C12=CC=CC=C2NC2=C1C=CC=C2C(=O)O DHHFGQADZVYGIE-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
Description
Verfahren zur Darstellung eines ltarhazolderivates. Durch das schweizerische Hauptpatent Nr. 140094 ist ein Verfahren zur Darstel lung eines Karbazolderivates geschützt, das dadurch gekennzeichnet ist, dass man 1 . 8- Dioxykarbazol-8.6-disulfosäure mit Hilfe einer Mineralsäure unter Druck in das 1 . 8 Dioxykarbazol überführt.
Es wurde nun gefunden, dass diese Reak tion nicht allein auf die Abspaltung von Sulfogruppen abgegrenzt ist, sondern dass man auch andere Gruppen, wie die Amino- gruppe, Carboxylgruppe, Halogen usw. aus substitutierten Aminokarbazolen, Karbazol- carbonsäuren, Halogenkarbazolen usw. nach bekannten Verfahren entfernen kann und so zu Karbazolderivaten, die teilweise auf an derem Wege überhaupt nicht oder nur sehr schwierig erhältlich sind, gelangt.
Gegenstand vorliegender Erfindung ist nun ein Verfahren zur Darstellung eines Kar- bazolderivates, dadurch gekennzeichnet, dass man 1-Oxykarbazol-2-carbonsäure durch Er hitzen in das 1-Oxykarbazol überführt.
<I>Beispiel:</I> 50 Gewichtsteile 1-Oxykarbazol-2-carbon- säure werden auf 280 bis 240 erhitzt, bis die Kohlensäureabspaltung beendet ist. 1VIan nimmt das Reaktionsprodukt mit verdünnter Natronlauge auf und fällt aus der filtrierten Lösung das 1-Oxykarbazol mit Mineralsäu ren aus. Nach Umkristallisieren aus verdünn tem Alkohol oder Ligroin erhält man es in farblosen Blättchen vom Schmelzpunkt 168 bis 164 . Es ist mit dem in der Literatur be schriebenen identisch<B>(</B>D. R. P. 258298) und soll als Ausgangsmaterial für Farbstoffe und Pharmazeutika Verwendung finden.
Process for the preparation of an itarhazole derivative. The main Swiss patent No. 140094 protects a process for the preparation of a carbazole derivative, which is characterized in that 1. 8-Dioxycarbazole-8.6-disulfonic acid with the help of a mineral acid under pressure in the 1. 8 Dioxykarbazole transferred.
It has now been found that this reaction is not limited to the splitting off of sulfo groups, but that other groups, such as the amino group, carboxyl group, halogen, etc., from substituted aminocarbazoles, carbazole carboxylic acids, halocarbazoles, etc. can also be used according to known methods Process can remove and thus arrive at carbazole derivatives, some of which are not at all or very difficult to obtain by other means.
The present invention now relates to a method for preparing a carbazole derivative, characterized in that 1-oxycarbazole-2-carboxylic acid is converted into 1-oxycarbazole by heating.
<I> Example: </I> 50 parts by weight of 1-oxycarbazole-2-carboxylic acid are heated to between 280 and 240 until the carbon dioxide has been split off. 1VIan absorbs the reaction product with dilute sodium hydroxide solution and precipitates 1-oxycarbazole with mineral acids from the filtered solution. After recrystallization from dilute alcohol or ligroin, it is obtained in colorless flakes with a melting point of 168 to 164. It is identical to the one described in the literature (D. R. P. 258298) and is intended to be used as a starting material for dyes and pharmaceuticals.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE143702X | 1928-01-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH143702A true CH143702A (en) | 1930-11-30 |
Family
ID=5669828
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH143702D CH143702A (en) | 1928-01-02 | 1928-08-30 | Process for the preparation of a carbazole derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH143702A (en) |
-
1928
- 1928-08-30 CH CH143702D patent/CH143702A/en unknown
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