CH156350A - Process for the preparation of a basic substituted carboxamide. - Google Patents
Process for the preparation of a basic substituted carboxamide.Info
- Publication number
- CH156350A CH156350A CH156350DA CH156350A CH 156350 A CH156350 A CH 156350A CH 156350D A CH156350D A CH 156350DA CH 156350 A CH156350 A CH 156350A
- Authority
- CH
- Switzerland
- Prior art keywords
- ethoxy
- preparation
- basic substituted
- substituted carboxamide
- quinolinecarboxylic
- Prior art date
Links
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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/50—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung eines basisch substituierten Carbonsäureauiids. Es wurde gefunden, dass man zu einem basisch substituierten Carbonsäureamid ge langen kann, wenn man einen reaktionsfähi gen Ester des Diäthylaminoäthanols auf ein Metallderivat des 2-Äthoxy-4-chinolincarbon- säureanilids einwirken lässt.
Das so erhaltene 2-Äthoxy-4-chinolin- carbonsäure- N -phenyl- N -diäthylaminoäthyl- amid bildet ein gelbliches Öl, vom Kp. o,5 205-210'. Das in Wasser schwer lösliche Perchlorat der Base schmilzt bei 160-r62 .
Die neue Verbindung soll zu therapeuti schen Zwecken Verwendung finden.
<I>Beispiel</I> 8,9 Teile 2-Äthoxy-4-chinolincarbonsäure- anilid (farblose Kristalle vom Smp. 180-1810, dargestellt aus 2-Chlor-4-chinolincarbonsäure- anilid und äthylalkoholisohem Natrium) wer den in 100 Teilen äylol mit 1,2 Teilen Natriumamid bis zur Beendigung der Ammo- niakentwicklung erwärmt. Nun fügt man 4,1 Teile Chloräthyldiäthylamin zu und er -wärmt weiter.
Nach erfolgter Umsetzung destilliert man das Lösungsmittel ab und nimmt den Rückstand in verdünnter Säure auf. Aus der filtrierten Lösung wird die Base mit Soda gefällt und in Äther aufge nommen. Nach Vertreiben des Lösungsmittels hinterbleibt das 2-Äthoxy-4-chinolincarbon- säure-N-phenyl-N-diäthylaminoäthylamid als gelbliches 01 vom Kp. o,5 205-2100.
An Stelle von Chloräthyldiäthylamin kön nen auch andere reaktionsfähige Ester des Diäthylaminoäthanols, zum Beispiel der Brom wasserstoff-, der Jodwasserstoff- oder der Toluolsulfosäureester Verwendung finden. Zur Herstellung der Metallverbindung des Carbon- säureamids kann man auch andere Metall amide, wie zum Beispiel Kalium- oder Kal- ziumamid, Metallalkoholate, wie zum Beispiel Natrium- oder galiumalkoholat oder reak tionsfähige Metalle wie zum Beispiel Natrium, Kalium usw. gebrauchen.
Process for the preparation of a basic substituted carboxylic acid eiide. It has been found that a basic substituted carboxamide can be obtained if a reactive ester of diethylaminoethanol is allowed to act on a metal derivative of 2-ethoxy-4-quinolinecarboxylic anilide.
The 2-ethoxy-4-quinoline-carboxylic acid-N-phenyl-N -diethylaminoethyl amide thus obtained forms a yellowish oil, with a boiling point of 0.5205-210 '. The perchlorate of the base, which is sparingly soluble in water, melts at 160-r62.
The new connection is intended to be used for therapeutic purposes.
<I> Example </I> 8.9 parts of 2-ethoxy-4-quinoline-carboxylic acid anilide (colorless crystals with a melting point of 180-1810, prepared from 2-chloro-4-quinoline-carboxylic acid anilide and ethyl alcohol isohem sodium) in 100 Parts of ethylene with 1.2 parts of sodium amide were heated until the evolution of ammonia ceased. Now 4.1 parts of chloroethyl diethylamine are added and the heating continues.
After the reaction has taken place, the solvent is distilled off and the residue is taken up in dilute acid. The base is precipitated from the filtered solution with soda and taken up in ether. After the solvent has been driven off, the 2-ethoxy-4-quinolinecarboxylic acid N-phenyl-N-diethylaminoethylamide remains as a yellowish oil with a boiling point of 0.5205-2100.
Instead of chloroethyl diethylamine, other reactive esters of diethylaminoethanol, for example hydrogen bromine, hydrogen iodide or toluenesulfonic acid ester, can also be used. Other metal amides, such as potassium or calcium amide, metal alcoholates such as sodium or galium alcoholate or reactive metals such as sodium, potassium, etc., can also be used to produce the metal compound of the carboxylic acid amide.
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH156350T | 1930-05-09 | ||
CH153033T | 1930-05-09 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH156350A true CH156350A (en) | 1932-07-31 |
Family
ID=25716108
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH156350D CH156350A (en) | 1930-05-09 | 1930-05-09 | Process for the preparation of a basic substituted carboxamide. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH156350A (en) |
-
1930
- 1930-05-09 CH CH156350D patent/CH156350A/en unknown
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