DE441707C - Process for the preparation of saturated and unsaturated dialkylamides of pyridine-3-carboxylic acid - Google Patents
Process for the preparation of saturated and unsaturated dialkylamides of pyridine-3-carboxylic acidInfo
- Publication number
- DE441707C DE441707C DEG63025D DEG0063025D DE441707C DE 441707 C DE441707 C DE 441707C DE G63025 D DEG63025 D DE G63025D DE G0063025 D DEG0063025 D DE G0063025D DE 441707 C DE441707 C DE 441707C
- Authority
- DE
- Germany
- Prior art keywords
- pyridine
- carboxylic acid
- saturated
- unsaturated
- preparation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Description
Verfahren zur Darstellung von gesättigten und ungesättigten Dialkylamiden der Pyridin-3-carbonsäure. Inder Patentschrift 351 085 ist ein Verfah-, ren zur Darstellung von Dialkylamiden der Pyridin-3-carbonsäure beschrieben, dadurch gekennzeichnet, daß man Pyridin-3-carbonsäure bzw. deren Halogenide, Anhydride oder Ester mit sekundären aliphatischen Aminen behandelt.Process for the preparation of saturated and unsaturated dialkylamides of pyridine-3-carboxylic acid. Patent 351 085 describes a process for the preparation of dialkylamides of pyridine-3-carboxylic acid, characterized in that pyridine-3-carboxylic acid or its halides, anhydrides or esters are treated with secondary aliphatic amines.
Es wurde nun gefunden, daß man zu gesättigten oder ungesättigten Dialkylamiden der Pyridin-3-carbonsäure in einfacher Weise und mit guter Ausbeute auch dadurch gelangen kann, daß man das Anhydrid der Pyridin-2, 3-dicarbonsäure (Chinolinsäureanhydrid) mit gesättigten oder ungesättigten Dialkylaminen umsetzt und die zunächst entstehenden Reaktionsprodukte durch Erhitzen in die entsprechenden gesättigten oder ungesättigten Pyridin-3-carbonsäuredialkylamide überführt und diese zweckmäßig unter vermindertem Druck destilliert.It has now been found that saturated or unsaturated dialkylamides can be obtained the pyridine-3-carboxylic acid in a simple manner and with good yield also as a result can get that the anhydride of pyridine-2, 3-dicarboxylic acid (quinolinic anhydride) reacts with saturated or unsaturated dialkylamines and the initially formed Reaction products by heating into the corresponding saturated or unsaturated Pyridine-3-carboxylic acid dialkylamides transferred and these appropriately under reduced Distilled pressure.
Bringt man Pyridin@2, 3-dicarbonsä.ureanhydrid z. B. mit Diäthylamin zur Reaktion so entsteht zunächst das Diäthylaminsalz des, 3-Diäthylamids der Pyridin-2, 3-dicarbonsäure: Dieses zerfällt beim Erhitzen in Pyridin-3-carbonsäurediäthylamid, Kohlensäure und Di-: äthylamin. Nach beendeter Kohlensäureabspaltung 'kann man das erhaltene Pyridin-3-carbonsäurediätliylamid gegebenenfalls unter vermindertem Druck destillieren.If you bring pyridine @ 2, 3-dicarbonsä.ureanhydrid z. B. with diethylamine for the reaction so first the diethylamine salt of, 3-diethylamide of pyridine-2, 3-dicarboxylic acid: This breaks down into pyridine-3-carboxylic acid diethylamide when heated, Carbonic acid and diethylamine. After the carbon dioxide has been split off, you can pyridine-3-carboxylic acid diethylamide obtained, if appropriate under reduced pressure distill.
Die Reaktion erfolgt nach folgendem Schema An Stelle von Diäthylamin können andere gesättigte oder ungesättigte sekundäre Amine, wie Dipropyl-, Diamyl-, Methylpropyl-, X.thylpropyl-, Diallylamin, Piperidin usw., Verwendung finden. Daß die Reaktion in obigem Sinne verlaufen würde, war nach dem, was über die Einwirkung von Ammoniak auf Pyridin-2, 3-dicarbonsäureanhydrid bekannt ist (vgl. Annalen 288 [1895] S. 255), nicht vorauszusehen. Einerseits bildet sich im letzteren Falle nicht ein 3-, sondern ein 2-Monamid der Pyridinz, 3-dicarbonsäure, und zwar ist hierbei der Reaktionsverlauf überhaupt nur bei Verwendung eines Lösungsmittels einigermaßen einheitlich. Anderseits tritt bei Erhitzung des Ammoniumsalzes des z-'Monamids der -Dicarbonsäure nicht Kohlensäureabspaltung ein; sondern es bildet sich unter Austritt von. Ammoniak und Wasser das idem P'hthalimid entsprechende Imid der Pyridin-z, 3-dicarbonsäure (vgl. a. a. O. S. 259 und 26o).The reaction takes place according to the following scheme Instead of diethylamine, other saturated or unsaturated secondary amines, such as dipropyl, diamyl, methylpropyl, ethylpropyl, diallylamine, piperidine, etc., can be used. According to what is known about the action of ammonia on pyridine-2,3-dicarboxylic acid anhydride (cf. Annalen 288 [1895] p. 255), it could not be foreseen that the reaction would proceed in the above sense. On the one hand, in the latter case, not a 3- but a 2-monamide of pyridine, 3-dicarboxylic acid is formed, and the course of the reaction is only somewhat uniform when using a solvent. On the other hand, when the ammonium salt of the z -'monamide of -dicarboxylic acid is heated, carbonic acid is not split off; but it forms with the emergence of. Ammonia and water, the imide of pyridine-z, 3-dicarboxylic acid corresponding to idem phthalimide (cf. aa OS 259 and 26o).
Gegenüber dem Verfahren der Patentschrift 351 o85 besitzt das vorliegende den Vorteil größerer Einfachheit und Kürze. Insbesondere kommt man hierbei ohne die Darstellung des Pyri,din-3-carbonsäureh'alogenids aus. Beispiel.Compared to the method of the patent 351 o85 has the present the advantage of greater simplicity and brevity. In particular, you get here without the representation of the pyri, din-3-carboxylic acid halide. Example.
I Teil Pyridin-2, 3-dicarbons;äureanhydid wird in 3 Teile Diäthylamineingetragen. Man kocht während 2 Stunden am Rückfluß und destilliert das überschüssige Diäthylamin ab. Der Rückstand wird bis auf I8o° erhitzt. Es erfolgt Entwicklung von Kohlensäure und Diäthylamin. Der ölige Rückstand wird nach beendeter Köhlensäureentwicklung bei vermindertem Druck destilliert, wobei das in der Patentschrift '35I 085 beschriebene Tyridin-3-carbonsäurediäthylamid als helles öl übergeht.I part of pyridine-2,3-dicarbons; acid anhydride is introduced into 3 parts of diethylamine. The mixture is refluxed for 2 hours and the excess diethylamine is distilled off. The residue is heated to 180 °. Carbon dioxide and diethylamine develop. After the evolution of carbonic acid has ceased, the oily residue is distilled under reduced pressure, the tyridine-3-carboxylic acid diethylamide described in patent specification '35I 085 passing over as a pale oil.
Ersetzt man im obigen Beispiel das Diäthylamin durch Dipropyl- oder Diamylamin oder Piperidin, so gelangt man zum Pyridin-3-carbonsäuredipropylamid, -,diamylamid oder -piperid, welche gleichfalls in der Patentschrift 35r o85 beschrieben sind.If in the above example the diethylamine is replaced by dipropyl or Diamylamine or piperidine, this leads to pyridine-3-carboxylic acid dipropylamide, -, diamylamide or piperide, which is also described in patent 35r085 are.
Auf dieselbe Weise werden Pyridin-3-carbonsäuredialkylamide mit ungesättigten und gemischten Alkylresten erhalten, z. B.: Pyridini3-carbonsäurediallylamid, ein wasserlösliches öl, das bei 147° unter 0,3 mm Druck siedet, Pyridin-3-carbonsäuremethylpropylamid, ein in Wasser leicht lösliches gelbliches öl vom Sdp. 17 4' unter - 16 mm Druck, Pyridin-3-carbonsäureäthylpropylamid, ebenfalls ein wasserlösliches öl vom Sdp. i73° unter 15 mm Druck.In the same way, pyridine-3-carboxylic acid dialkylamides with unsaturated and mixed alkyl radicals are obtained, e.g. B .: Pyridini3-carbonsäurediallylamid, a water-soluble oil, boiling at 147 ° at 0.3 mm pressure, pyridin-3-carbonsäuremethylpropylamid, an easily soluble in water yellowish oil, bp 17 4 'below -. 1 mm 6 Pressure, pyridine -3-carbonsäureäthylpropylamid, also a water-soluble oil, bp. I73 ° under 1 5 mm pressure.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEG63025D DE441707C (en) | 1924-12-28 | 1924-12-28 | Process for the preparation of saturated and unsaturated dialkylamides of pyridine-3-carboxylic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEG63025D DE441707C (en) | 1924-12-28 | 1924-12-28 | Process for the preparation of saturated and unsaturated dialkylamides of pyridine-3-carboxylic acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE441707C true DE441707C (en) | 1927-03-10 |
Family
ID=7133168
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEG63025D Expired DE441707C (en) | 1924-12-28 | 1924-12-28 | Process for the preparation of saturated and unsaturated dialkylamides of pyridine-3-carboxylic acid |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE441707C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4782157A (en) * | 1984-12-03 | 1988-11-01 | American Cyanamid Co. | Preparation of substituted and unsubstituted 2-carbamoyl nicotinic and 3-quinolinecarboxylic acids |
-
1924
- 1924-12-28 DE DEG63025D patent/DE441707C/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4782157A (en) * | 1984-12-03 | 1988-11-01 | American Cyanamid Co. | Preparation of substituted and unsubstituted 2-carbamoyl nicotinic and 3-quinolinecarboxylic acids |
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