CH192996A - Process for the preparation of a quinoline compound. - Google Patents
Process for the preparation of a quinoline compound.Info
- Publication number
- CH192996A CH192996A CH192996DA CH192996A CH 192996 A CH192996 A CH 192996A CH 192996D A CH192996D A CH 192996DA CH 192996 A CH192996 A CH 192996A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- compound
- quinoline compound
- diaminochinaldine
- gray
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 title description 2
- -1 quinoline compound Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 4
- VEFLKXRACNJHOV-UHFFFAOYSA-N 1,3-dibromopropane Chemical compound BrCCCBr VEFLKXRACNJHOV-UHFFFAOYSA-N 0.000 claims description 3
- 241000894006 Bacteria Species 0.000 claims description 3
- 239000008280 blood Substances 0.000 claims description 3
- 210000004369 blood Anatomy 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 244000045947 parasite Species 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Darstellung einer Chinolinverbindnng. Gegenstand des Hauptpatentes ist ein Verfahren zur Herstellung einer Verbindung von folgender Formel
EMI0001.0003
welches dadurch gekennzeichnet ist, dass man 4,6-Diaminochinaldin auf Epichlorhydrin einwirken lässt. Diese Verbindung zeichnet sich durch hohe Wirksamkeit gegen Bak terien und Blutparasiten aus.
Es wurde nun ,gefunden, dass man eine Verbindung von folgender Formel
EMI0001.0012
welche die gleiche pharmakologische Wir kung aufweist, herstellen kann, wenn man 4,6-Diaminochinaldin auf Trimethylenbro- mid zur Einwirkung bringt.
Das Endprodukt ist ein graugelbes Pul ver, welches sehr wirksam gegen Bakterien und Blutparasiten ist und- das als Heilmittel Verwendung finden soll. Beispiel:
EMI0002.0002
7 g 4;6-Diaminochinaldin werden in 30 cm' Alkohol mit 4 g Trimethylenbromid wie im Beispiel des Zusatzpatentes Nr. 191,460 um gesetzt; auch das Reaktionsprodukt wird ebenso verarbeitet.
Die rohe Base obiger Zu- sammensetzung, die ein dunkles Harz bildet, wird in verdünnter Essigsäure gelöst, die Lösung salzsauer gemacht und das Hydro- chlorid durch Zugabe von Chlornatrium lösung gefällt. Es bildet ein graugelbes Pulver, das beim Erwärmen sich leicht in Wasser löst mit gelber Farbe. Die aus der Lösung durch Natronlauge als flockiger, grauer Niederschlag gefällte Base verwan delt sich bei 115 in eine schaumige Masse, die bei weiterem Erhitzen allmählich ein dunkles Harz bildet.
Process for the preparation of a quinoline compound. The main patent relates to a process for the preparation of a compound of the following formula
EMI0001.0003
which is characterized in that 4,6-diaminochinaldine is allowed to act on epichlorohydrin. This compound is highly effective against bacteria and blood parasites.
It has now been found that one can obtain a compound of the following formula
EMI0001.0012
which has the same pharmacological effect, can be produced if 4,6-diaminochinaldine is brought into action on trimethylene bromide.
The end product is a gray-yellow powder which is very effective against bacteria and blood parasites and which should be used as a remedy. Example:
EMI0002.0002
7 g of 4; 6-diaminochinaldine are reacted in 30 cm 'of alcohol with 4 g of trimethylene bromide as in the example of additional patent no. 191,460; the reaction product is also processed.
The crude base of the above composition, which forms a dark resin, is dissolved in dilute acetic acid, the solution is made hydrochloric and the hydrochloride is precipitated by adding sodium chloride solution. It forms a gray-yellow powder that easily dissolves in water when heated with a yellow color. The base precipitated from the solution by sodium hydroxide solution as a fluffy, gray precipitate turns at 115 into a foamy mass which gradually forms a dark resin on further heating.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH192996T | 1935-05-28 | ||
| CH186669T | 1935-05-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH192996A true CH192996A (en) | 1937-09-15 |
Family
ID=25721404
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH192996D CH192996A (en) | 1935-05-28 | 1935-05-28 | Process for the preparation of a quinoline compound. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH192996A (en) |
-
1935
- 1935-05-28 CH CH192996D patent/CH192996A/en unknown
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