CH131496A - Process for the preparation of 6-isopropyloxy-8-aminoquinoline. - Google Patents
Process for the preparation of 6-isopropyloxy-8-aminoquinoline.Info
- Publication number
- CH131496A CH131496A CH131496DA CH131496A CH 131496 A CH131496 A CH 131496A CH 131496D A CH131496D A CH 131496DA CH 131496 A CH131496 A CH 131496A
- Authority
- CH
- Switzerland
- Prior art keywords
- aminoquinoline
- isopropyloxy
- preparation
- amino group
- oxy
- Prior art date
Links
- MJNOQKOSXTUHHG-UHFFFAOYSA-N 6-propan-2-yloxyquinolin-8-amine Chemical compound C(C)(C)OC=1C=C2C=CC=NC2=C(C=1)N MJNOQKOSXTUHHG-UHFFFAOYSA-N 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 230000001754 anti-pyretic effect Effects 0.000 claims description 2
- 239000008280 blood Substances 0.000 claims description 2
- 210000004369 blood Anatomy 0.000 claims description 2
- 230000002147 killing effect Effects 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 244000045947 parasite Species 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- -1 benzal group Chemical group 0.000 description 2
- 235000010650 Hyssopus officinalis Nutrition 0.000 description 1
- 240000001812 Hyssopus officinalis Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- ZIQRIAYNHAKDDU-UHFFFAOYSA-N sodium;hydroiodide Chemical compound [Na].I ZIQRIAYNHAKDDU-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Darstellung von 6-Isopropylogy-8-aminoehinolin. Irn schweizerischen Patent Nr. 126723 i1: ein Verfahren zur Darstellung von 6- Isopropyloxy -8-a.minochinolin beschrieben, welches darin besteht, da.ss man 6-Oxy-8- a.minochinolin mit einem isopropylierend ,irkenden Mittel behandelt.
Gemäss dem Verfahren der vorliegenden Erfindung wird diese Verbindung hergestellt durch Isop.ropylierung der Hydroxylgruppe eines, 6'-Oxy-8-aminochinolinsi, das in. der Aminogruppe einen abspaltbaren Substituen- ten, z.
B. eine I'ormyl- oder eine Benzal- gruppe besitzt, worauf man aus dem so er haltenen Derivat des 6-Isopropyloxy-8- arninochinolins den Substituenten der Amino- (rruppe abspaltet.
Das 6-Isopropzrloxy-8-aminochinolin hat antipyretische Eigenschaften und ausserdem noch eine starke spezifisch abtötende Wir kung auf Blutparasiten und soll als Heil mittel, sowie als Zwischenprodukt zur Her- Stellung pharmazeutisch wertvoller Derivate verwendet werden.
<I>Beispiel</I> 188 -r 6-Oxy-8-formylaminochinolin wer den in eine Lösung von 2'3 gr Natrium in drei Litern Alkohol eingetragen. Hierzu werden<B>170</B> gr Jodisopropyl gegeben und vier Stunden am Rückfluss gekocht. Vom ge bildeten Jodnatrium wird abgesaugt, der Al kohol abdestilliert, der Rückstand in Äther aufgenommen und mehrfach mit Natron lauge, zuletzt mit Wasser, gewaschen. Nach dem Abdestillieren des Äthers wird der Rückstand in drei Litern verdünnter Schwe felsäure gelöst und vier bis sechs Stunden am Rüekfluss gekocht.
Nach dem Neutra- lisieren mit Soda wird ausgeäthert, die äthe rische Lösung gründlich mit Natronlauge und Wasser gewaschen, hierauf nach dem Trocknen der Äther abdestilliert.
Das gebildete 6-Isopropyloxy-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 in Wasser ziemlich schwer lös liches, gelbes, kristallines Chlorhydrat.
Process for the preparation of 6-isopropylogy-8-aminoehinoline. In Swiss patent no. 126723 i1: a process for the preparation of 6-isopropyloxy-8-a.minoquinoline is described, which consists in treating 6-oxy-8-a.minoquinoline with an isopropylating agent.
According to the process of the present invention, this compound is prepared by isop.ropylation of the hydroxyl group of a 6'-oxy-8-aminoquinoline which has a removable substituent in the amino group, e.g.
B. has a I'ormyl or a benzal group, whereupon the substituent of the amino group is split off from the derivative of 6-isopropyloxy-8-arninochinoline obtained in this way.
The 6-isopropzrloxy-8-aminoquinoline has antipyretic properties and also has a strong specific killing effect on blood parasites and is intended to be used as a remedy and as an intermediate for the manufacture of pharmaceutically valuable derivatives.
<I> Example </I> 188 -r 6-Oxy-8-formylaminoquinoline are added to a solution of 2'3 grams of sodium in three liters of alcohol. For this purpose <B> 170 </B> g iodoisopropyl are added and refluxed for four hours. The sodium iodine formed is filtered off with suction, the alcohol is distilled off, the residue is taken up in ether and washed several times with sodium hydroxide solution, finally with water. After distilling off the ether, the residue is dissolved in three liters of dilute sulfuric acid and boiled for four to six hours on the reflux.
After neutralization with soda, ether is extracted, the ethereal solution is washed thoroughly with sodium hydroxide solution and water, and then, after drying, the ether is distilled off.
The 6-isopropyloxy-8-aminoquinoline formed boils at 149 to 150 under a pressure of 2 mm. It is a light yellow, thick liquid and, with hydrochloric acid, forms a yellow, crystalline hydrochloric acid which is rather poorly soluble in water.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH128225T | 1926-04-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH131496A true CH131496A (en) | 1929-02-15 |
Family
ID=4386689
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH131496D CH131496A (en) | 1926-04-13 | 1926-04-13 | Process for the preparation of 6-isopropyloxy-8-aminoquinoline. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH131496A (en) |
-
1926
- 1926-04-13 CH CH131496D patent/CH131496A/en unknown
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