CH201872A - Process for the preparation of 3,6-diamino-10-methylacridinium glycolate. - Google Patents
Process for the preparation of 3,6-diamino-10-methylacridinium glycolate.Info
- Publication number
- CH201872A CH201872A CH201872DA CH201872A CH 201872 A CH201872 A CH 201872A CH 201872D A CH201872D A CH 201872DA CH 201872 A CH201872 A CH 201872A
- Authority
- CH
- Switzerland
- Prior art keywords
- diamino
- preparation
- glycolate
- methylacridinium
- water
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- -1 3,6-diamino-10-methylacridinium glycolate Chemical compound 0.000 title description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- RARHFIBGFUOOML-UHFFFAOYSA-N acridine;hydrate Chemical compound O.C1=CC=CC2=CC3=CC=CC=C3N=C21 RARHFIBGFUOOML-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
Description
Verfahren zur Herstellung von 3,0-Diamino-10-methylacridiniumglykolat. Die vorliegende Erfindung bezieht sich auf ein Verfahren zur Herstellung von 3;6- Diamino-10-m-etllylacridiniumglykol,at, wel- ches .dadurch gekennzeichnet ist, @daZ man 3,6 Diamino--10 -methylacridiniumzyklohexanon- verbindung mit Wasser kocht und das so entstehende Acridiniumhydroxyd mit Glykol- säure umsetzt.
Das so erhältliche @3,6-Diamino-10-methyl- acridiniumglykolatstellt ein rotbraunes Pul ver dar, das in Äther, Benzol und Chloroform unlöslich, in Aceton schwer löslich und in Äthanol, Methanol und Wasser leicht 1ö lieh ist; es soll für pharmazeutische Zwecke Ver wendung finden.
<I>Beispiel:</I> 320 ,g 3,6-Di@amino-10-methylaeridinium- zykloh,exanonverbindung werden am abstei genden Kühler mit 10 Liter Wasser und etwas Tierkohle :gekocht. Dabei wird durch Einleiten von Stickstoff die Luft verdrängt, um Oxydation der Ammoniumbase ,zu ver hindern.
Wenn alles Zyklohexanon abd es@til- liert ist, gibt man 76 g Glykolsäure zu, fil- triert und dampft im Vakuum zur Trockne. Durch Aufnehmen in Alkohol und Fällen mit Aceton und Äther erhält man ein rot braunes Pulver. Daus 3,6-Diamino-l0-znethyl- acridiniumglykolat löst sich in Alkohol und Essigester.
In Äther, Aceton und Benzol ist es unlöslich, in Wasser löst es sichspielend leicht.
Process for the preparation of 3,0-diamino-10-methylacridinium glycolate. The present invention relates to a process for the production of 3; 6- diamino-10-m-ethyllacridiniumglycol, ate, which is characterized by boiling 3.6 diamino-10-methylacridiniumcyclohexanone compound with water and the resulting acridinium hydroxide is reacted with glycolic acid.
The thus obtainable @ 3,6-diamino-10-methyl-acridiniumglykolat is a red-brown powder which is insoluble in ether, benzene and chloroform, sparingly soluble in acetone and easily borrowed in ethanol, methanol and water; it is intended to be used for pharmaceutical purposes.
<I> Example: </I> 320, g of 3,6-Di @ amino-10-methylaeridinium- cycloh, exanone compound are boiled on the descending cooler with 10 liters of water and some animal charcoal. The air is displaced by introducing nitrogen in order to prevent oxidation of the ammonium base.
When all the cyclohexanone has been removed, 76 g of glycolic acid are added, the mixture is filtered and evaporated to dryness in vacuo. A red-brown powder is obtained by absorption in alcohol and precipitation with acetone and ether. The 3,6-diamino-10-methyl acridinium glycolate dissolves in alcohol and ethyl acetate.
It is insoluble in ether, acetone and benzene; in water it dissolves easily.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE201872X | 1935-04-20 | ||
| CH197431T | 1936-04-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH201872A true CH201872A (en) | 1938-12-15 |
Family
ID=25722988
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH201872D CH201872A (en) | 1935-04-20 | 1936-04-18 | Process for the preparation of 3,6-diamino-10-methylacridinium glycolate. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH201872A (en) |
-
1936
- 1936-04-18 CH CH201872D patent/CH201872A/en unknown
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