CH209505A - Process for the preparation of an indophenol-like compound of the naphthocarbazole series. - Google Patents
Process for the preparation of an indophenol-like compound of the naphthocarbazole series.Info
- Publication number
- CH209505A CH209505A CH209505DA CH209505A CH 209505 A CH209505 A CH 209505A CH 209505D A CH209505D A CH 209505DA CH 209505 A CH209505 A CH 209505A
- Authority
- CH
- Switzerland
- Prior art keywords
- compound
- indophenol
- naphthocarbazole
- series
- preparation
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 7
- 238000000034 method Methods 0.000 title claims description 4
- KYUOHCDPIQOFBD-UHFFFAOYSA-N 11h-naphtho[2,1-a]carbazole Chemical class C1=CC2=CC=CC=C2C(C=C2)=C1C1=C2C2=CC=CC=C2N1 KYUOHCDPIQOFBD-UHFFFAOYSA-N 0.000 title claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
Landscapes
- Indole Compounds (AREA)
Description
Verfahren zur Herstellung einer indophenolartigen Verbindung der Naphthocarbazolreihe. Nach dem im Hauptpatent beschriebenen Verfahren erhält man eine indophenolartige Verbindung, wenn man 3.4.5.6-Dinaphtho- carbazol mit p-Chinonchlorimid zur Umsetzung bringt.
Wie nun weiter gefunden wurde, erhält man einen Endstoff mit ähnlichen Eigen schaften, wenn man N-Methyl-3.4.5.6- dinaphthocarbazol mit p-Chinonchlorimid zur Umsetzung bringt.
<I>Beispiel:</I> 14 Teile N-Methyl-3.4.6.6-Dinaphtho- carbazol (Beispiel 2 des DRP Nr. 624563), er halten durch Umsetzung von 2.2'-Dioxy- 1.1'-dinaphthyl mit Methylamin werden in 150 Volumteilen Schwefelsäure von<B>60'</B> Bö bei -<B>100</B> gelöst und mit einer auf die gleiche Temperatur gekühlten Lösung von 10,6 Teilen p-Chinonchlorimid in 100 Volum- teilen Schwefelsäure versetzt.
Nach kurzer Zeit wird die tiefblaue Lösung auf Eis unter Zugabe von Hydrosulfit ausgerührt. Die er- haltene hellgelbe Leukoverbindung löst sich in verdün nterNatriumhydroxydlösung schwerer als die entsprechende Verbindung aus 3.4.<B>0'.</B> 6- Dinaphthocarbazol, leicht dagegen bei Zusatz einer geringen Menge Äthylalkohol. Chlor lauge oxydiert zum blauen Indokörper.
Der Endstoff ist ein Zwischenprodukt für die Herstellung von Farbstoffen.
Process for the preparation of an indophenol-like compound of the naphthocarbazole series. According to the process described in the main patent, an indophenol-like compound is obtained if 3.4.5.6-dinaphthocarbazole is reacted with p-quinone chlorimide.
As has now been found further, an end product with similar properties is obtained if N-methyl-3.4.5.6-dinaphthocarbazole is reacted with p-quinone chlorimide.
<I> Example: </I> 14 parts of N-methyl-3.4.6.6-dinaphtho-carbazole (Example 2 of DRP No. 624563), obtained by reacting 2.2'-dioxy-1.1'-dinaphthyl with methylamine are in 150 parts by volume of sulfuric acid of <B> 60 '</B> gust at - <B> 100 </B> and mixed with a solution, cooled to the same temperature, of 10.6 parts of p-quinone chlorimide in 100 parts by volume of sulfuric acid.
After a short time, the deep blue solution is stirred on ice with the addition of hydrosulfite. The light yellow leuco compound obtained is more difficult to dissolve in dilute sodium hydroxide solution than the corresponding compound from 3.4. <B> 0 '. </B> 6- Dinaphthocarbazole, on the other hand it dissolves easily when a small amount of ethyl alcohol is added. Chlorine alkali oxidizes to the blue indo body.
The end product is an intermediate product for the manufacture of dyes.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE209505X | 1938-04-13 | ||
| CH206720T | 1938-08-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH209505A true CH209505A (en) | 1940-04-15 |
Family
ID=25724336
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH209505D CH209505A (en) | 1938-04-13 | 1938-08-13 | Process for the preparation of an indophenol-like compound of the naphthocarbazole series. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH209505A (en) |
-
1938
- 1938-08-13 CH CH209505D patent/CH209505A/en unknown
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