CH124930A - Process for the preparation of 6-methoxy- (a-dimethylamino-y-methyl-propyl) -8-aminoquinoline. - Google Patents
Process for the preparation of 6-methoxy- (a-dimethylamino-y-methyl-propyl) -8-aminoquinoline.Info
- Publication number
- CH124930A CH124930A CH124930DA CH124930A CH 124930 A CH124930 A CH 124930A CH 124930D A CH124930D A CH 124930DA CH 124930 A CH124930 A CH 124930A
- Authority
- CH
- Switzerland
- Prior art keywords
- aminoquinoline
- methoxy
- dimethylamino
- methyl
- propyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 3
- YGGTVPCTAKYCSQ-UHFFFAOYSA-N 6-methoxyquinolin-8-amine Chemical compound N1=CC=CC2=CC(OC)=CC(N)=C21 YGGTVPCTAKYCSQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- -1 6-methoxy (α-dimethylamino-γ-methyl-propyl) -8-aminoquinoline Chemical compound 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OVOWTANBDBUKBN-UHFFFAOYSA-N 1-chloro-n,n-dimethylbutan-1-amine Chemical compound CCCC(Cl)N(C)C OVOWTANBDBUKBN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- DJEQZVQFEPKLOY-UHFFFAOYSA-N N,N-dimethylbutylamine Chemical group CCCCN(C)C DJEQZVQFEPKLOY-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Darstellung von 6-Methoay-(a-Dimethylamino-r-methyl-propyl)-8- aminochinolin. Gegenstand vorliegender Erindung ist ein Verfahren zur Darstellung von 6-Methoxy (a-Dimethylamino-y-methyl-propyl)-8-amino- chinolin. Das Verfahren ist dadurch gekenn zeichnet,
dass man 6-Methoxy-8-aminochino- lin mit einem in y-Stellung durch einen reak tionsfähigen Substituenten substituierten a- Dimethylamino-butan zur Umsetzung bringt.
Die neue Verbindung bildet ein gelbes 01 mit dem Siedepunkt 192 bis 194 C bei 1,5 mm Druck und soll als therapeutisch au sserordentlich wertvolles, spezifisch wirksames Heilmittel Verwendung finden.
Beispiel: Zur Darstellung von 6-Methoxy-(a-Dime- thylamino-y-methyl-propyl) - 8-aminochinolin
EMI0001.0019
werden 174 Gewichtsteile 6-Methoxy-8-ami- nochinolin mit 185,5 Gewichtsteilen a-Dime- thylamino-y-methyl-propylchlorid während 8 bis 10 Stunden auf 130 bis 140' C erhitzt. Das Reaktionsprodukt wird inWasser gelöst, alkalisch gemacht und die ausgeschiedene Base in Äther aufgenommen. Die neue Ver bindung destilliert als gelbes 01 bei 192 bis 194' bei 1,5 mm Druck.
Die Darstellung dieser Verbindung kann auch erfolgen, indem man .die beiden Komponenten bei Gegenwart eines Lösungsmittels, verdünnter Alkohol oder Wasser, auf Kochtemperatur erhitzt. Ebenso kann auch an Stelle des freien Chlorides dessen Chlorhydrat oder der entsprechende p- Toluolsulfosäureester beziehungsweise dessen Chlorhydrat zur Anwendung gelangen.
Process for the preparation of 6-methoay- (a-dimethylamino-r-methyl-propyl) -8-aminoquinoline. The present invention is a process for the preparation of 6-methoxy (α-dimethylamino-γ-methyl-propyl) -8-aminoquinoline. The procedure is characterized by
6-methoxy-8-aminoquinoline is reacted with an α-dimethylamino-butane substituted in the y-position by a reactive substituent.
The new compound forms a yellow oil with a boiling point of 192 to 194 C at 1.5 mm pressure and is intended to be used as a therapeutically extraordinarily valuable, specifically effective remedy.
Example: For the preparation of 6-methoxy- (a-dimethylamino-y-methyl-propyl) - 8-aminoquinoline
EMI0001.0019
174 parts by weight of 6-methoxy-8-aminoline with 185.5 parts by weight of α-dimethylamino-γ-methyl-propyl chloride are heated to 130 to 140 ° C. for 8 to 10 hours. The reaction product is dissolved in water, made alkaline and the precipitated base is taken up in ether. The new compound distilled as a yellow 01 at 192 to 194 'at 1.5 mm pressure.
This compound can also be prepared by heating the two components to boiling temperature in the presence of a solvent, dilute alcohol or water. Likewise, instead of the free chloride, its chlorohydrate or the corresponding p-toluenesulfonic acid ester or its chlorohydrate can be used.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE124930X | 1924-09-11 | ||
| CH123059T | 1925-08-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH124930A true CH124930A (en) | 1928-03-01 |
Family
ID=25710001
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH124930D CH124930A (en) | 1924-09-11 | 1925-08-08 | Process for the preparation of 6-methoxy- (a-dimethylamino-y-methyl-propyl) -8-aminoquinoline. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH124930A (en) |
-
1925
- 1925-08-08 CH CH124930D patent/CH124930A/en unknown
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