DE544621C - Process for the preparation of 2- or 3-oxycarbazole - Google Patents
Process for the preparation of 2- or 3-oxycarbazoleInfo
- Publication number
- DE544621C DE544621C DEI38562D DEI0038562D DE544621C DE 544621 C DE544621 C DE 544621C DE I38562 D DEI38562 D DE I38562D DE I0038562 D DEI0038562 D DE I0038562D DE 544621 C DE544621 C DE 544621C
- Authority
- DE
- Germany
- Prior art keywords
- oxycarbazole
- preparation
- lead oxide
- tube
- methoxycarbazole
- 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
Links
- 238000000034 method Methods 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- 229910000464 lead oxide Inorganic materials 0.000 claims description 5
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 claims description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000011521 glass Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000008262 pumice Substances 0.000 description 2
- GUBGUXGKVFBTRZ-UHFFFAOYSA-N 1-methoxy-9H-carbazole Chemical compound C12=CC=CC=C2NC2=C1C=CC=C2OC GUBGUXGKVFBTRZ-UHFFFAOYSA-N 0.000 description 1
- BISIQSCKDZYPLR-UHFFFAOYSA-N 3-methoxy-9H-carbazole Chemical compound C1=CC=C2C3=CC(OC)=CC=C3NC2=C1 BISIQSCKDZYPLR-UHFFFAOYSA-N 0.000 description 1
- LJUKCUCBMZNDOR-UHFFFAOYSA-N 6-methoxy-2,3,4,9-tetrahydro-1H-carbazole Chemical compound C1CCCC2=C1NC1=CC=C(OC)C=C12 LJUKCUCBMZNDOR-UHFFFAOYSA-N 0.000 description 1
- OIQBXVKUOQCCHA-UHFFFAOYSA-N 7-ethoxy-2,3,4,9-tetrahydro-1H-carbazole Chemical compound C1CCCC2=C1C1=CC=C(OCC)C=C1N2 OIQBXVKUOQCCHA-UHFFFAOYSA-N 0.000 description 1
- 229910001369 Brass Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000010951 brass Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Description
Verfahren zur Darstellung von 2- bzw. 3-Oxycarbazol Es %vurde gefunden, daß man aus 7- bzw. 6-Alkoxytetrahydrocarbazolen unter Abspaltung der Alkylgruppen zu 2- bzw. 3-Oxycarbazol gelangt, wenn man diese Produkte bei 5oo bis 6oo° mit Bleioxyd behandelt. Dieses Verfahren führt gegenüber der bekannten Einwirkung von Dehydrierungsmitteln auf hydrierte Alkoxycarbazole überraschenderweise direkt zu den entsprechenden Oxyverbindungen und stellt gegenüber den bisher üblichen Herstellungsverfahren für Oxycarbazole einen wesentlichen technischen Fortschritt dar.Process for the preparation of 2- or 3-oxycarbazole It was found that that from 7- or 6-alkoxytetrahydrocarbazoles with elimination of the alkyl groups 2- or 3-oxycarbazole is obtained when these products are mixed with lead oxide at 50 to 600 ° treated. This method leads to the known exposure to dehydrating agents on hydrogenated alkoxycarbazoles surprisingly directly to the corresponding oxy compounds and contrasts with the conventional manufacturing processes for oxycarbazoles represents a significant technical advance.
Das so erhältliche 2- bzw. 3-Okycarbazol soll zur Darstellung von anderen Zwischenprodukten und Farbstoffen Verwendung finden. Beispiel 2o Gewichtsteile 6-Methoxytetrahydrocarbazol werden mit 7o Gewichtsteilen Bleioxyd innig gemischt und in eine Glasröhre eingefüllt; der Rest der Röhre wird dann mit Bieioxydbimssteinstückchen angefüllt. Die Glasröhre wird in eine Messingröhre oder in eine Röhre aus gebranntem Ton geschoben, um so eine gleichmäßige Erhitzung zu erzielen. Bei 5oo bis 6oo° wird die Destillation derart vorgenommen, daß man zuerst das vorgelegte Bleioxydbimssteingemisch gut anheizt und dann die Substanz schnell, zweckmäßig im inerten Gasstrom, wie Kohlensäure oder Stickstoff, über das Bleioxyd destilliert. Das gewonnene Produkt wird in verdünnter Natronlauge gelöst und ausgefällt. Durch Umkristallisieren aus Xylol erhält man das 3-Oxycarbazol in weißen Nadeln vom F. P. 256°. Mit dem in der Literatur beschriebenen 3-Oxycarbazol ist es in jeder Beziehung identisch. Das durch Methylierung nach den üblichen Methoden aus ihm erhaltene 3-Methoxycarbazol kristallisiert aus Alkohol in weißen Nadeln vom F. P. 142'. Es ist ebenfalls mit dem in der Literatur bekannten Methoxycarbazol identisch.The 2- or 3-okycarbazole obtainable in this way is intended to represent other intermediates and dyes are used. Example 2o parts by weight 6-Methoxytetrahydrocarbazole are intimately mixed with 7o parts by weight of lead oxide and filled into a glass tube; the rest of the tube is then covered with bits of bi-oxide pumice filled. The glass tube is put into a brass tube or into a tube made of fired Clay pushed in order to achieve even heating. At 5oo to 6oo ° it becomes the distillation is carried out in such a way that the lead oxide pumice stone mixture is first introduced heats up well and then the substance quickly, expediently in an inert gas stream, such as carbonic acid or nitrogen, distilled over the lead oxide. The product obtained is diluted in Sodium hydroxide solution dissolved and precipitated. Recrystallization from xylene gives the 3-oxycarbazole in white needles from the F. P. 256 °. With the one described in the literature 3-Oxycarbazole is identical in every respect. That by methylation after the 3-Methoxycarbazole obtained from it crystallizes from alcohol using customary methods in white needles from F. P. 142 '. It is also the same as that known in the literature Methoxycarbazole identical.
In analoger Weise kann auch das 2-Oxycarbazol aus dem 7-Äthoxytetrahydrocarbazol erhalten werden.In an analogous manner, 2-oxycarbazole can also be obtained from 7-ethoxytetrahydrocarbazole can be obtained.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI38562D DE544621C (en) | 1929-06-30 | 1929-06-30 | Process for the preparation of 2- or 3-oxycarbazole |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI38562D DE544621C (en) | 1929-06-30 | 1929-06-30 | Process for the preparation of 2- or 3-oxycarbazole |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE544621C true DE544621C (en) | 1932-02-19 |
Family
ID=7189811
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEI38562D Expired DE544621C (en) | 1929-06-30 | 1929-06-30 | Process for the preparation of 2- or 3-oxycarbazole |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE544621C (en) |
-
1929
- 1929-06-30 DE DEI38562D patent/DE544621C/en not_active Expired
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