CH166494A - Process for the preparation of a derivative of 2-oxy-5.6-dihydro-7.8-benzocarbazole. - Google Patents
Process for the preparation of a derivative of 2-oxy-5.6-dihydro-7.8-benzocarbazole.Info
- Publication number
- CH166494A CH166494A CH166494DA CH166494A CH 166494 A CH166494 A CH 166494A CH 166494D A CH166494D A CH 166494DA CH 166494 A CH166494 A CH 166494A
- Authority
- CH
- Switzerland
- Prior art keywords
- dihydro
- oxy
- benzocarbazole
- preparation
- carbazole
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000002253 acid Substances 0.000 claims description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 5
- 230000020477 pH reduction Effects 0.000 claims description 5
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- -1 alkali metal salt Chemical class 0.000 claims description 3
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 2
- 150000008041 alkali metal carbonates Chemical class 0.000 claims description 2
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 2
- 229910002092 carbon dioxide Inorganic materials 0.000 claims 1
- 239000001569 carbon dioxide Substances 0.000 claims 1
- 239000000975 dye Substances 0.000 claims 1
- 239000013067 intermediate product Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- AJDMRZYTDUHZFT-UHFFFAOYSA-N 13-azatetracyclo[8.7.0.02,7.011,16]heptadeca-1(10),2,4,6,8,11(16),12,14-octaene Chemical compound C1=CC=CC=2C=CC=3C=4C=NC=CC4CC3C21 AJDMRZYTDUHZFT-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
Landscapes
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Darstellung eines Abkömmlings des 2-Ogy-6.6-dihydro-7.8- benzocarbazols. Es wurde gefunden, dass man die 2-Oxy- 5. 6 - dihydro - 7. 8 - carbazol - 3 - carbonsäure dadurch erhalten kann, dass man auf ein Al kalisalz des 2-Oxy - 5 . 6 - dihydro- 7 . 8 - benzo- carbazols Kohlensäure unter Druck bei er höhter Temperatur einwirken lässt und die freie Säure durch Ansäuern abscheidet.
Eine Abänderung des Verfahrens besteht darin, dass man das freie 2-Oxy-5.6-dihydro- 7.8-benzocarbazol unter Zusatz eines Alkali- carbonats mit Kohlensäure unter Druck und bei erhöhter Temperatur behandelt, wobei sich intermediär das Alkalisalz des Carbazols bildet. Aus der wässerigen Lösung der Schmelze kann die gebildete Carbonsäure durch An säuern abgeschieden werden.
<I>Beispiel:</I> 10 Gewichtsteile 5.6-dibydro-7.8-benzo- carbazol-2-sulfoiisaures Natrium werden mit 1.5 Gewichtsteilen gepulvertem Kaliumhydro- xyd gemischt und solange bei<B>270-2800</B> C geschmolzen, bis keine Sulfonsäure mehr nachweisbar ist. Nach dem Erkalten wird mit Wasser aufgenommen und von alkaliun- löslichen Nebenprodukten abfiltriert. Aus dem Filtrat fällt beim Ansäuern das 2-Oxy-5.6- dihydro-7.8-benzocarbazol kristallinisch aus. Es ist leicht löslich in heissem Alkohol und schmilzt bei<B>1830</B> C.
Ein Gemisch von 1 Gewichtsteil des so erhaltenen 2-Oxy- 5 . 6 -dihydro-7 . 8-benzocar- bazols und 3 Gewichtsteilen Pottasche wird 10 Stunden unter einem Kohlensäuredruck von 50 Atmosphären bei<B>2600</B> C gehalten. Nach dem Erkalten wird das Reaktionspro dukt in Wasser aufgenommen, mit Salzsäure kongosauer gestellt, abgesaugt und gewaschen. Darauf wird es mit Soda in heissem Wasser gelöst und filtriert.
Aus dem Filtrat fällt beim Ansäuern die gelb gefärbte 2-Oxy-5. 6- dihydro-7.8-benzocarbazol-3-carbonsäure. Die Alkalisalze sind in kaltem Wasser ziemlich schwer löslich, in heissem Wasser leicht lös lich. Die freie Säure verliert oberhalb 220 C Kohlensäure. Der Zersetzungspunkt ist nicht scharf.
Process for the preparation of a derivative of 2-Ogy-6.6-dihydro-7.8-benzocarbazole. It has been found that the 2-oxy-5, 6-dihydro-7, 8-carbazole-3-carboxylic acid can be obtained by using an alkali metal salt of 2-oxy-5. 6 - dihydro- 7. 8 - benzo-carbazole lets carbonic acid take effect under pressure at an elevated temperature and the free acid is separated off by acidification.
A modification of the process consists in treating the free 2-oxy-5,6-dihydro-7,8-benzocarbazole with the addition of an alkali metal carbonate with carbonic acid under pressure and at elevated temperature, the alkali metal salt of carbazole being formed as an intermediate. The carboxylic acid formed can be deposited from the aqueous solution of the melt by acidification.
<I> Example: </I> 10 parts by weight of 5.6-dibydro-7.8-benzo-carbazole-2-sulfoic acid sodium are mixed with 1.5 parts by weight of powdered potassium hydroxide and melted at <B> 270-2800 </B> C until until no more sulfonic acid can be detected. After cooling, it is taken up with water and alkali-insoluble by-products are filtered off. The 2-oxy-5.6-dihydro-7.8-benzocarbazole precipitates in crystalline form from the filtrate on acidification. It is easily soluble in hot alcohol and melts at <B> 1830 </B> C.
A mixture of 1 part by weight of the 2-oxy-5 thus obtained. 6-dihydro-7. 8-benzocarbazoles and 3 parts by weight of potash are kept at <B> 2600 </B> C for 10 hours under a carbonic acid pressure of 50 atmospheres. After cooling, the reaction product is taken up in water, made Congo acidic with hydrochloric acid, filtered off with suction and washed. It is then dissolved in hot water with soda and filtered.
On acidification, the yellow colored 2-oxy-5 falls from the filtrate. 6- dihydro-7.8-benzocarbazole-3-carboxylic acid. The alkali salts are rather sparingly soluble in cold water and easily soluble in hot water. The free acid loses carbonic acid above 220 C. The decomposition point is not sharp.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE166494X | 1932-02-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH166494A true CH166494A (en) | 1934-01-15 |
Family
ID=5685821
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH166494D CH166494A (en) | 1932-02-18 | 1933-02-14 | Process for the preparation of a derivative of 2-oxy-5.6-dihydro-7.8-benzocarbazole. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH166494A (en) |
-
1933
- 1933-02-14 CH CH166494D patent/CH166494A/en unknown
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