CH126722A - Process for the preparation of 6-ethoxy-8-aminoquinoline. - Google Patents
Process for the preparation of 6-ethoxy-8-aminoquinoline.Info
- Publication number
- CH126722A CH126722A CH126722DA CH126722A CH 126722 A CH126722 A CH 126722A CH 126722D A CH126722D A CH 126722DA CH 126722 A CH126722 A CH 126722A
- Authority
- CH
- Switzerland
- Prior art keywords
- aminoquinoline
- ethoxy
- chlorohydrate
- preparation
- properties
- Prior art date
Links
Description
Verfahren zur Darstellung -von 6-Äthoxy-8-aminoehinolin. Aminoderivate von Alkoxychinolinen sind bekannt, zum Beispiel das 5-Amino-S- äthoxychinolin (D. R. P. Nr. 60308, 65102, 65111), dessen N-Acetylverbindung bemer kenswerte antipyretische Eigenschaften auf weist.
Es wurde nun gefunden, dass das bisher noch unbekannte 6-Äthoxy-8-aminocliinolin ausser den schon erwähnten antipyretischen Eigenschaften des 5-Amine-8-äthoxychinolins auch noch eine starke spezifisch abtötende Wirkung auf Blutparasiten ausübt.
Gemäss dem Verfahren der vorliegenden Erfindung wird diese Verbindung hergestellt durch Äthylierung der Hydroxylgruppe des Ei-Oxy-8-aminochinolins.
Das 6-Äthoxy-8-aminochinolin soll so wohl selbst als Heilmittel, sowie auch als Zwischenprodukt zur Herstellung pharma zeutisch wertvoller Derivate Verwendung finden. Beispiel:
EMI0001.0019
160 Gewichtsteile 6-Oxy-8-aminochinolin werden in 400 Gewichtsteilen 10 %iger Na tronlauge unter Rühren gelöst und in die klare Lösung 154 Gewichtsteile Diäthyl- sulfat eingetragen. Die Flüssigkeit erwärmt sich. Nach Beendigung der Reaktion werden nochmals 400 Gewichtsteile 10 %iger Natron lauge zugefügt und kurz aufgekocht.
Die <B>L</B> alkalische Reaktionsmasse wird ausgeäthert, die Ätherlösung mit Natronlauge und darauf mit Wasser nochmals ausgeschüttelt. Der Äther wird nach dem Trocknen mit Pott asche. verdampft und der Rückstand frak tioniert. Das 6-Äthoxy-8-aminochinolin de stilliert bei einem Druck von zirka 1 mm bei 144 bis 145 . Das gelbe ölige Destillat erstarrt rasch zu einer derben Kristallmasse vom Schmelzpunkt -f- 60 .
Das Chlorhydrat dieser Verbindung zeigt sehr ähnliche Eigen schaften in bezug auf Farbe und Löslichkeit, wie .das Chlorhydrat des 6-Methoxy-8-amino- chinolins.
Process for the preparation of 6-ethoxy-8-aminoehinoline. Amino derivatives of alkoxyquinolines are known, for example 5-amino-Sethoxyquinoline (D. R. P. No. 60308, 65102, 65111), the N-acetyl compound has remarkable antipyretic properties.
It has now been found that the hitherto unknown 6-ethoxy-8-aminocliinoline, in addition to the aforementioned antipyretic properties of 5-amine-8-ethoxyquinoline, also has a strong specific killing effect on blood parasites.
According to the process of the present invention, this compound is prepared by ethylation of the hydroxyl group of egg-oxy-8-aminoquinoline.
The 6-ethoxy-8-aminoquinoline is supposed to be used as a remedy itself, as well as as an intermediate for the production of pharmaceutically valuable derivatives. Example:
EMI0001.0019
160 parts by weight of 6-oxy-8-aminoquinoline are dissolved in 400 parts by weight of 10% strength sodium hydroxide solution with stirring and 154 parts by weight of diethyl sulfate are added to the clear solution. The liquid heats up. After the reaction has ended, another 400 parts by weight of 10% strength sodium hydroxide solution are added and the mixture is briefly boiled.
The <B> L </B> alkaline reaction mass is extracted with ether, the ethereal solution is extracted again with sodium hydroxide solution and then with water. After drying, the ether becomes ash with pot. evaporated and the residue fractionated. The 6-ethoxy-8-aminoquinoline de stills at a pressure of about 1 mm at 144 to 145. The yellow oily distillate quickly solidifies into a coarse crystal mass with a melting point of -f- 60.
The chlorohydrate of this compound shows properties in terms of color and solubility that are very similar to those of the chlorohydrate of 6-methoxy-8-aminoquinoline.
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE126722X | 1925-04-29 | ||
CH125476T | 1926-04-13 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH126722A true CH126722A (en) | 1928-07-02 |
Family
ID=25710476
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH126722D CH126722A (en) | 1925-04-29 | 1926-04-13 | Process for the preparation of 6-ethoxy-8-aminoquinoline. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH126722A (en) |
-
1926
- 1926-04-13 CH CH126722D patent/CH126722A/en unknown
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