AT146819B - Process for the preparation of diaminoquinolines. - Google Patents
Process for the preparation of diaminoquinolines.Info
- Publication number
- AT146819B AT146819B AT146819DA AT146819B AT 146819 B AT146819 B AT 146819B AT 146819D A AT146819D A AT 146819DA AT 146819 B AT146819 B AT 146819B
- Authority
- AT
- Austria
- Prior art keywords
- preparation
- diaminoquinolines
- filtered
- water
- hot
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- MAROONSWSSXHPU-UHFFFAOYSA-N quinoline-2,3-diamine Chemical class C1=CC=C2N=C(N)C(N)=CC2=C1 MAROONSWSSXHPU-UHFFFAOYSA-N 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000005011 4-aminoquinolines Chemical class 0.000 description 1
- IBWOBEUJEJNYOA-UHFFFAOYSA-N 6-nitroquinolin-2-amine Chemical compound C1=C([N+]([O-])=O)C=CC2=NC(N)=CC=C21 IBWOBEUJEJNYOA-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 201000004792 malaria Diseases 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- WECFWBJFIOOXPR-UHFFFAOYSA-N quinoline-2,6-diamine Chemical compound N1=C(N)C=CC2=CC(N)=CC=C21 WECFWBJFIOOXPR-UHFFFAOYSA-N 0.000 description 1
- IKWVYRACZMFUHI-UHFFFAOYSA-N quinoline-4,6-diamine Chemical compound N1=CC=C(N)C2=CC(N)=CC=C21 IKWVYRACZMFUHI-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
<Desc/Clms Page number 1>
Verfahren zur Darstellung von Diaminochinolineu.
Es wurde gefunden, dass man zu wertvollen Produkten gelangt, wenn man primäre Bz-Nitro-2- oder-4-aminochinoline reduziert. Die so erhältlichen Diaminochinoline unterscheiden sich von den in der deutschen Patentschrift Nr. 536447 beschriebenen, ebenfalls durch Reduktion von Bz-Nitroaminochinolinen erhältlichen Diaminochinolinen chemisch schon dadurch, dass sie im Pyridinkern eine Aminogruppe enthalten. Ferner unterscheiden sie sieh auch in therapeutischer Hinsicht ; während die nach dem bekannten Verfahren darstellbaren Verbindungen als Malaria-Heilmittel verwendet werden, sollen die nach dem vorliegenden Verfahren gewinnbaren Produkte als Harn-sowie Gewebsdesinfizientien Verwendung finden.
EMI1.1
wird unter Rühren und Erwärmen im Wasserbad mit 5 eisenpulver reduziert.
Nach einer halben Stunde wird heiss filtriert, das Filtrat ammoniakalisch gemacht und wieder filtriert ; hierauf wird das klare Filtrat salzsauer gemacht und eingedampft. Die konzentrierte Lösung wird sodann mit starker Natronlauge übersättigt, das hiebei ausgefällte 4. 6-Diaminochinolin abgesaugt und mit Wasser gewaschen. Nach dem Umkristallisieren aus Benzol und wenig Äthanol bildet es ein farbloses feines Pulver, das bei 2150 unter Dunkelfärbung schmilzt ; Ausbeute 2 g. Charakteristisch ist die stark grüne Fluoreszenz von verdünnten, schwach sauren Lösungen, die auf Zusatz von überschüssiger Mineralsäure verschwindet. Das blassgelbe Dihydrochlorid ist in Wasser leicht, in Äthanol schwer löslich.
Beispiel 2 : 11-4 g 6-Nitro-2-aminochinolin (B. 58 [1925] 806) gelöst in 150 cm3 Äthanol, werden bei etwa 40 mit Palladium und Wasserstoff reduziert ; nach 3-4 Stunden ist die Reduktion beendet.
Nachdem durch stärkeres Erwärmen völlige Lösung erfolgt ist, wird vom Katalysator abfiltriert, das Filtrat mit alkoholischer Salzsäure angesäuert und mit Äther versetzt, wobei sich 13 g des in Wasser leicht löslichen Dihydrochlorid des 2. 6-Diaminochinolins ausscheiden. Zur Reinigung wird es in heissem Wasser gelöst, die heisse Lösung schwach ammoniakalisch gemacht, mit etwas Tierkohle behandelt und heiss filtriert. Die beim Erkalten auskristallisierende Base bildet schwach graugelbe Nadeln, die bei 2190 unter Dunkelfärbung schmelzen. Die wässerige Lösung der Base reagiert gegen Phenolphtalein nur schwach alkalisch im Gegensatz zu dem im Beispiel 1 beschriebenen 4.6-Isomeren.
**WARNUNG** Ende DESC Feld kannt Anfang CLMS uberlappen**.
<Desc / Clms Page number 1>
Process for the preparation of diaminochinolineu.
It has been found that valuable products are obtained by reducing primary Bz-nitro-2 or 4-aminoquinolines. The diamino quinolines obtainable in this way differ chemically from the diamino quinolines described in German Patent No. 536447, also obtainable by reduction of Bz-nitroaminoquinolines, in that they contain an amino group in the pyridine nucleus. They also make a difference in therapeutic terms; While the compounds that can be prepared by the known method are used as malaria remedies, the products that can be obtained by the present method are intended to be used as urinary and tissue disinfectants.
EMI1.1
is reduced with iron powder while stirring and heating in a water bath.
After half an hour, the mixture is filtered hot, the filtrate is made ammoniacal and filtered again; the clear filtrate is then made acidic and evaporated. The concentrated solution is then supersaturated with strong sodium hydroxide solution, and the 4,6-diaminoquinoline which has precipitated out is filtered off with suction and washed with water. After recrystallization from benzene and a little ethanol, it forms a colorless, fine powder which melts at 2150 while turning dark; Yield 2g. The strong green fluorescence of dilute, weakly acidic solutions is characteristic, and disappears when excess mineral acid is added. The pale yellow dihydrochloride is easily soluble in water and sparingly soluble in ethanol.
Example 2: 11-4 g of 6-nitro-2-aminoquinoline (B. 58 [1925] 806) dissolved in 150 cm3 of ethanol are reduced at about 40 cm with palladium and hydrogen; the reduction is complete after 3-4 hours.
After complete dissolution has taken place by increasing the temperature, the catalyst is filtered off, the filtrate is acidified with alcoholic hydrochloric acid and ether is added, 13 g of the dihydrochloride of 2,6-diaminoquinoline, which is readily soluble in water, separating out. To clean it, it is dissolved in hot water, the hot solution is made weakly ammoniacal, treated with a little animal charcoal and filtered while hot. The base, which crystallizes out on cooling, forms pale gray-yellow needles which melt at 2190 and turn dark. The aqueous solution of the base reacts only slightly alkaline to phenolphthalein, in contrast to the 4,6-isomer described in Example 1.
** WARNING ** End of DESC field may overlap beginning of CLMS **.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE146819X | 1932-01-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AT146819B true AT146819B (en) | 1936-08-25 |
Family
ID=5671585
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT146819D AT146819B (en) | 1932-01-26 | 1933-01-20 | Process for the preparation of diaminoquinolines. |
Country Status (1)
| Country | Link |
|---|---|
| AT (1) | AT146819B (en) |
-
1933
- 1933-01-20 AT AT146819D patent/AT146819B/en active
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