CH125626A - Process for the preparation of 6-isopropyloxy-8-aminoquinoline. - Google Patents
Process for the preparation of 6-isopropyloxy-8-aminoquinoline.Info
- Publication number
- CH125626A CH125626A CH125626DA CH125626A CH 125626 A CH125626 A CH 125626A CH 125626D A CH125626D A CH 125626DA CH 125626 A CH125626 A CH 125626A
- Authority
- CH
- Switzerland
- Prior art keywords
- isopropyloxy
- aminoquinoline
- production
- hydrochloric acid
- preparation
- Prior art date
Links
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Darstellung von 6-Isopropyloxy-8-aminochinolin. Amino-Derivate von Alkoxy-Chinolinen sind bekannt, zum Beispiel das 5-Amino-8- äthoxychinolin (D. R. P. 60808, 65102, 65111), dessen N-Acetylverbindung bemer kenswerte antipyretische Eigenschaften auf weist.
Es wurde nun gefunden, dass das bisher noch unbekannte 6-Isopropyloxy-8-amino- chinolin ausser den schon erwähnten anti- pyretischen Eigenschaften des 5-Amino-8- äthoxychinolins auch noch eine starke spezi fisch abtötende Wirkung auf Blutparasiten ausübt.
Gemäss dem Verfahren der vorliegenden Erfindung wird diese Verbindung erhalten durch Reduktion eines 6-Isopropyloxychino- lins, welches in 8-Stellung einen zur Amino- CY ruppe reduzierbaren stickstoffhaltigen Sub- stituenten aufweist. zum Beispiel durch Re duktion von 6-Isoprö-pyloxy-8-nitrochinolin oder von 6-Isopropyloxy-8-azoarylchinolin.
Das 6-Isopropyloxy-8-aminochinolin soll sowohl selbst als Heilmittel, sowie auch als Zwischenprodukt zur Herstellung pharma- zeutisch wertvoller Derivate Verwendung finden.
Beispiel:
EMI0001.0028
5,0 kg 6-Isopropyloxy-8-nitrochinolin werden in 20 Litern reiner konzentrierter Salzsäure gelöst und warm eingegossen in 60 Liter einer Zinnchlorürlösung, die 600 gr Zinnchlorür in I. Liter Lösung enthält. Nach einstündigem Erhitzen auf -f- 100 werden 100 Liter konzentrierter Salzsäure zuge geben, das nach .dem Erkalten abgeschiedene Chlorzinndoppelsalz abgesaugt, mit Salz säure gewaschen und in üblicher Weise zer legt.
Das so erhaltene 6-Isopropy loxy-8-amino- chinolin siedet unter einem Druck von 2 mm bei 149 bis 150 . Es stellt eine hellgelbe, dicke Flüssigkeit dar und bildet mit Salz- säure ein im Wasser ziemlich schwer lös liches, gelbes, kristallines Chlorhydrad.
Process for the preparation of 6-isopropyloxy-8-aminoquinoline. Amino derivatives of alkoxy quinolines are known, for example 5-amino-8-ethoxyquinoline (D. R. P. 60808, 65102, 65111), the N-acetyl compound of which has remarkable antipyretic properties.
It has now been found that the hitherto unknown 6-isopropyloxy-8-aminoquinoline, in addition to the aforementioned antipyretic properties of 5-amino-8-ethoxyquinoline, also has a strong specific killing effect on blood parasites.
According to the process of the present invention, this compound is obtained by reducing a 6-isopropyloxyquinoline which has a nitrogen-containing substituent which can be reducible to the amino-CY group in the 8-position. for example by reducing 6-isopropyloxy-8-nitroquinoline or 6-isopropyloxy-8-azoarylquinoline.
The 6-isopropyloxy-8-aminoquinoline is said to be used both as a medicinal product itself and as an intermediate for the production of pharmaceutically valuable derivatives.
Example:
EMI0001.0028
5.0 kg of 6-isopropyloxy-8-nitroquinoline are dissolved in 20 liters of pure concentrated hydrochloric acid and poured warm into 60 liters of a tin chloride solution containing 600 g of tin chloride in 1 liter of solution. After heating to -f- 100 for one hour, 100 liters of concentrated hydrochloric acid are added, and the chlorotin double salt which separates out after cooling is suctioned off, washed with hydrochloric acid and decomposed in the usual way.
The 6-isopropyloxy-8-aminoquinoline obtained in this way boils at 149 to 150 under a pressure of 2 mm. It is a light yellow, thick liquid and, together with hydrochloric acid, forms a yellow, crystalline hydrochloride that is rather poorly soluble in water.
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE125626X | 1925-04-29 | ||
CH121343T | 1926-04-13 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH125626A true CH125626A (en) | 1928-04-16 |
Family
ID=25709667
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH125626D CH125626A (en) | 1925-04-29 | 1926-04-13 | Process for the preparation of 6-isopropyloxy-8-aminoquinoline. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH125626A (en) |
-
1926
- 1926-04-13 CH CH125626D patent/CH125626A/en unknown
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