CH125625A - Process for the preparation of 6-ethoxy-8-aminoquinoline. - Google Patents
Process for the preparation of 6-ethoxy-8-aminoquinoline.Info
- Publication number
- CH125625A CH125625A CH125625DA CH125625A CH 125625 A CH125625 A CH 125625A CH 125625D A CH125625D A CH 125625DA CH 125625 A CH125625 A CH 125625A
- Authority
- CH
- Switzerland
- Prior art keywords
- aminoquinoline
- ethoxy
- production
- hydrochloric acid
- ethoxyquinoline
- Prior art date
Links
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Darstellung von 6-Äthogy-8-aminochinolin. Amino-Derivate von Alkoxy-Chinolinen sind bekannt, zum Beispiel das 5-Amino-8- äthoxychinolin (D. R. P. 60808, 6510?, 65111), dessen N-Acetylverbindung bemerkenswerte a.ntipyretische Eigenschaften aufweist.
Es wurde nun gefunden, dass das bisher noch unbekannte 6-Ätlioxy-8-aminochinolin ausser den schon erwähnten antipyretischen Eigenschaften des 5-Amino-8-äthoxychinolins ueb. noch eine starke spezifisch abtötende a Wirkung auf Blutparasiten ausübt.
Gemäss dem Verfahren der vorliegenden Erfindung wird diese Verbindung erhalten durch Reduktion eines 6-Äthoxychinolins, das in 8-Stellung einen zur Aminogruppe redu zierbaren, stickstoffhaltigen Substituenten aufweist, zum Beispiel durch Reduktion von 6- .#.tlioxy -8-nitrochinolin oder von 6-Äthoxy- 8-a.zo-aiylchinolin.
Das 6-Äthoxy-8-aminochinolin soll sowohl selbst als Heilmittel, sowie auch als Zwi schenprodukt zur Herstellung pharmazeutisch wertvoller Derivate Verwendung finden.
EMI0001.0024
5,0 kg 6-Äthoxy-8-nitrochinolin werden in ?0 Litern reiner konzentrierter Salzsäure gelöst und warm eingegossen in 60 Liter einer Zinnchlorürlösung, die 600 gr Zinnchlorür in 1 Liter Lösung enthält.
Nach einstündigem Erhitzen auf -I- 100 werden 100 Liter kon zentrierter Salzsäure zugegeben, das nach dem Erkalten abgeschiedene Chlorzinndoppelsalz abgesaugt, mit Salzsäure gewaschen und in üblicher Weise zerlegt.
Da.s so gebildete 6-Äthoxy-8-aminochino- lin destilliert bei einem Druck von zirka 1 mm bei 144 bis 145 . Das gelbe, ölige De stillat erstarrt rasch zu einer derben Kristall masse vom Schmelzpunkt -I- 60 . Mit Salz säure bildet es ein orangefarbenes, in kaltem Wasser schwer lösliches, schön kristallisier tes Chlorhydrat. Das 6-Äthoxy-8-nitrochinolin kann ent sprechend dem 6-Methoxy-8-nitrochinolin ge wonnen werden (s. Hauptpatent Nr. 121343).
Process for the preparation of 6-ethogy-8-aminoquinoline. Amino derivatives of alkoxy quinolines are known, for example 5-amino-8-ethoxyquinoline (D. R. P. 60808, 6510 ?, 65111), the N-acetyl compound of which has remarkable antipyretic properties.
It has now been found that the hitherto unknown 6-Ätlioxy-8-aminochinolin except for the already mentioned antipyretic properties of 5-amino-8-ethoxyquinoline ueb. nor has a strong specific killing a effect on blood parasites.
According to the process of the present invention, this compound is obtained by reducing a 6-ethoxyquinoline which has a nitrogen-containing substituent in the 8-position which can be reduced to the amino group, for example by reducing 6-. #. Tlioxy-8-nitroquinoline or 6 Ethoxy-8-a.zo-aiylquinoline
The 6-ethoxy-8-aminoquinoline is said to be used both as a remedy and as an intermediate product for the production of pharmaceutically valuable derivatives.
EMI0001.0024
5.0 kg of 6-ethoxy-8-nitroquinoline are dissolved in? 0 liters of pure concentrated hydrochloric acid and poured warm into 60 liters of a tin chloride solution that contains 600 grams of tin chloride in 1 liter of solution.
After heating to -I- 100 for one hour, 100 liters of concentrated hydrochloric acid are added, and the chlorotin double salt which has separated out after cooling is filtered off with suction, washed with hydrochloric acid and broken down in the usual way.
The 6-ethoxy-8-aminochinolin thus formed distills at a pressure of about 1 mm at 144 to 145. The yellow, oily distillate quickly solidifies to form a coarse crystal mass with a melting point of -I- 60. With hydrochloric acid it forms an orange-colored, nicely crystallized chlorohydrate, which is poorly soluble in cold water. The 6-ethoxy-8-nitroquinoline can be obtained accordingly to the 6-methoxy-8-nitroquinoline (see main patent no. 121343).
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE125625X | 1925-04-29 | ||
CH121343T | 1926-04-13 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH125625A true CH125625A (en) | 1928-04-16 |
Family
ID=25709666
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH125625D CH125625A (en) | 1925-04-29 | 1926-04-13 | Process for the preparation of 6-ethoxy-8-aminoquinoline. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH125625A (en) |
-
1926
- 1926-04-13 CH CH125625D patent/CH125625A/en unknown
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