CH160945A - Process for the preparation of N-acetyl-2-ethoxy-3-nitrocarbazole. - Google Patents
Process for the preparation of N-acetyl-2-ethoxy-3-nitrocarbazole.Info
- Publication number
- CH160945A CH160945A CH160945DA CH160945A CH 160945 A CH160945 A CH 160945A CH 160945D A CH160945D A CH 160945DA CH 160945 A CH160945 A CH 160945A
- Authority
- CH
- Switzerland
- Prior art keywords
- acetyl
- ethoxy
- nitrocarbazole
- preparation
- ethoxycarbazole
- Prior art date
Links
- HBVNUAWAOOCOKI-UHFFFAOYSA-N 1-(2-ethoxy-3-nitrocarbazol-9-yl)ethanone Chemical compound C(C)(=O)N1C2=CC=CC=C2C=2C=C(C(=CC12)OCC)[N+](=O)[O-] HBVNUAWAOOCOKI-UHFFFAOYSA-N 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 230000000802 nitrating effect Effects 0.000 claims description 3
- -1 N-acetyl-2-ethoxycarbazole Chemical compound 0.000 claims description 2
- 150000001875 compounds Chemical group 0.000 claims description 2
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- YITQNMNIXPIYKZ-UHFFFAOYSA-N 1-(3-methoxy-6-nitrocarbazol-9-yl)ethanone Chemical compound C(C)(=O)N1C2=CC=C(C=C2C=2C=C(C=CC12)OC)[N+](=O)[O-] YITQNMNIXPIYKZ-UHFFFAOYSA-N 0.000 description 1
- HLDWAEXQOLMKDU-UHFFFAOYSA-N 1-(3-methoxycarbazol-9-yl)ethanone Chemical compound C1=CC=C2C3=CC(OC)=CC=C3N(C(C)=O)C2=C1 HLDWAEXQOLMKDU-UHFFFAOYSA-N 0.000 description 1
- FTYFSEUAYLAVPR-UHFFFAOYSA-N 2-ethoxy-9h-carbazole Chemical compound C1=CC=C2C3=CC=C(OCC)C=C3NC2=C1 FTYFSEUAYLAVPR-UHFFFAOYSA-N 0.000 description 1
- LWQPXVAMIFRUNQ-UHFFFAOYSA-N CCOC(C(N)=C1)=CC2=C1C1=CC=CC=C1N2 Chemical compound CCOC(C(N)=C1)=CC2=C1C1=CC=CC=C1N2 LWQPXVAMIFRUNQ-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- ICGLOTCMOYCOTB-UHFFFAOYSA-N [Cl].[Zn] Chemical compound [Cl].[Zn] ICGLOTCMOYCOTB-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Landscapes
- Indole Compounds (AREA)
Description
Verfahren zur Darstellung von N-Acetyl-2-äthoay-3-nitrokarbazol. Im Hauptpatent ist ein Verfahren zur Darstellung von N-Acetyl-6.nitro-3-methoxy- karbazol beschrieben, das dadurch gekenn zeichnet ist, dass man N-Acetyl-3-methoxykar- bazol mit einem nitrierenden Mittel behandelt.
Gegenstand vorliegender Erfindung ist nun ein Verfahren zur Herstellung des bisher noch nicht bekannten N-Acetyl-2-äthoxy-3- nitrokarbazols, dadurch gekennzeichnet, dass man N-Acetyl-2-äthoxykarbazol mit einem nitrierenden Mittel behandelt.
Man kann auch ein Acetylderivat ver wenden, das in Essigsäureanhydrid mit Chlor zink hergestellt wurde und dann ohne den Acetylkörper zu isolieren, die Nitrierung in demselben Lösungsmittel durchführen.
Die Verbindung soll als Zwischenprodukt in der Farbenindustrie Verwendung finden. <I>Beispiel:</I> 211 Gewichtsteile 2-Äthoxykarbazol wer den in 950 Gewichtsteilen Essigsäureanhydrid gelöst. Zur siedenden Lösung gibt man 3 Ge wichtsteile Chlorzink und lässt noch eine Stunde sieden. Die auf 50 abgekühlte Lö sung wird langsam unter gutem Rühren mit 70 cm3 Salpetersäure (d = 1,4), die mit 70 cm' Essigsäureanhydrid verdünnt sind, versetzt.
Das in gelben Nadeln ausgeschiedene N-Acetyl-2-äthoxy-3-nitrokarbazol schmilzt nach dem Umkristallisieren aus Toluol bei <B>178'.</B> Das daraus erhältliche 2-Äthoxy-3- aminokarbazol kristallisiert aus Anilin in farblosen Nadeln vom Schmelzpunkt 234'.
Das N-Acetyl-2-äthoxy-3-nitrokarbazol kann durch Kochen mit alkoholischer Kali lauge entacetyliert werden.
Process for the preparation of N-acetyl-2-ethoxy-3-nitrocarbazole. The main patent describes a process for the preparation of N-acetyl-6-nitro-3-methoxy-carbazole, which is characterized in that N-acetyl-3-methoxy-carbazole is treated with a nitrating agent.
The present invention now relates to a process for the preparation of the hitherto unknown N-acetyl-2-ethoxy-3-nitrocarbazole, characterized in that N-acetyl-2-ethoxycarbazole is treated with a nitrating agent.
You can also use an acetyl derivative that was prepared in acetic anhydride with chlorine zinc and then carry out the nitration in the same solvent without isolating the acetyl body.
The compound is intended to be used as an intermediate in the paint industry. <I> Example: </I> 211 parts by weight of 2-ethoxycarbazole are dissolved in 950 parts by weight of acetic anhydride. 3 parts by weight of zinc chloride are added to the boiling solution and the mixture is left to boil for another hour. The solution, cooled to 50, is slowly mixed with 70 cm 3 of nitric acid (d = 1.4) diluted with 70 cm of acetic anhydride, with thorough stirring.
The N-acetyl-2-ethoxy-3-nitrocarbazole separated in yellow needles melts after recrystallization from toluene at <B> 178 '. </B> The 2-ethoxy-3-aminocarbazole obtainable therefrom crystallizes from aniline in colorless needles from Melting point 234 '.
The N-acetyl-2-ethoxy-3-nitrocarbazole can be deacetylated by boiling with alcoholic potassium hydroxide solution.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE160945X | 1930-07-22 | ||
| CH156443T | 1931-07-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH160945A true CH160945A (en) | 1933-03-31 |
Family
ID=25716774
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH160945D CH160945A (en) | 1930-07-22 | 1931-07-21 | Process for the preparation of N-acetyl-2-ethoxy-3-nitrocarbazole. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH160945A (en) |
-
1931
- 1931-07-21 CH CH160945D patent/CH160945A/en unknown
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