CH306538A - Process for the preparation of a new pyridine-3,5-dicarboxylic acid derivative. - Google Patents
Process for the preparation of a new pyridine-3,5-dicarboxylic acid derivative.Info
- Publication number
- CH306538A CH306538A CH306538DA CH306538A CH 306538 A CH306538 A CH 306538A CH 306538D A CH306538D A CH 306538DA CH 306538 A CH306538 A CH 306538A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- dicarboxylic acid
- preparation
- acid derivative
- pyridine
- Prior art date
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
- C07D213/82—Amides; Imides in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Description
Verfahren zur Herstellung eines neuen Pyridin-3,5-diearbonsäure-Derivl">s, Das vorliegende Patent bezieht sich auf ein Verfahren zur Herstellung eines neuen Pyridin-3,5-dicarbonsäure-Derivates, nämlich des Pyridin-3,5-diearbonsä.ure-3-methylester-5- diäthylam.ids.
Dieses Verfahren ist. dadurch gekennzeieh- net, dass man eine Verbindung der Formel
EMI0001.0009
iri weleher X einen reaktionsfähigen, leicht ab spaltbaren Rest, beispielsweise das Hydroxyl-, ein Alkoxy-, ein Acyloxy radikal, ein Halogen atom oder ein Azidoradikal, bedeutet, mit Di- äthylamin umsetzt.
Der Umsatz geschieht vorzugsweise in An wesenheit eines Lösungs- bzw. Verdünnungs mittels und evtl. in Gegenwart eines Konden sationsmittels.
Das so erhaltene Pyridin-3,5-dicarbon- säure-3-metliylester-5-diäthylamid bildet weisse Nädelehen, welche bei 47-48 schmelzen.
Es soll als Zwischenprodukt zur Herstel- hmg von Arzneimitteln Verwendung finden. <I>Beispiel:</I> Das aus 18 g Pyridin-3,5-dicarbonsäure- monomethyIester und 150 em3 Thionylchlorid erhaltene Pyridin-3,5-dicarbonsäure-3-methyl- ester-5-elilorid (F.74-75 ) wird in 100 cms abs. Äther und 100 em3 abs. Benzol.
gelöst und unter Schütteln und Kühlen portio e eise mit einer Misehung von 25 cm3 abs. Diäthyl- amin mit 100 em3 abs. Benzol versetzt. Es scheidet sich sofort. Diäthylamin-chlorhydrat aus. Es wird noch 3/4 Stunden unter Feuehtig- keitsabschluss turbiniert und dann das ausge schiedene Diäthylamin-chlorhydrat abgesogen und mit Äther gewaschen.
Die vereinigten Äther-Benzollösungen werden mit 150 cm3 gesättigter Kaliumbicarbonatlösung geschüt telt, mit N atriiunsulfat getrocknet und zur Trockne verdampft. Der ölige Rückstand wird aus 350 ein?, Petroläther 60/90 unter Zusatz von Kohle umkristallisiert.
Man erhält 16 g des bei 47-48 schmelzenden Pyridin-3,5-di- carbonsäure-3-methylester-5-diäthylamids. Die neue Verbindung kristallisiert in farblosen dünnen Nadeln und löst sich leicht in Wasser und organischen Lösungsmitteln, mit Aus nahme von Petroläther, aus dem sie gut um kristallisiert werden kann.
Process for the preparation of a new pyridine-3,5-dicarboxylic acid derivative The present patent relates to a process for the preparation of a new pyridine-3,5-dicarboxylic acid derivative, namely pyridine-3,5-dicarboxylic acid. ure-3-methylester-5-diethylam.ids.
This procedure is. characterized in that a compound of the formula
EMI0001.0009
iri which X is a reactive, easily cleavable radical, for example the hydroxyl, an alkoxy, an acyloxy radical, a halogen atom or an azido radical, is reacted with diethylamine.
The conversion takes place preferably in the presence of a solvent or diluent and possibly in the presence of a condensation agent.
The pyridine-3,5-dicarboxylic acid-3-methylester-5-diethylamide thus obtained forms white needle loops which melt at 47-48.
It is to be used as an intermediate product in the manufacture of drugs. <I> Example: </I> The pyridine-3,5-dicarboxylic acid 3-methyl-ester-5-eliloride obtained from 18 g pyridine-3,5-dicarboxylic acid monomethyl ester and 150 cm3 thionyl chloride (F.74-75 ) is in 100 cms abs. Ether and 100 em3 abs. Benzene.
dissolved and while shaking and cooling portio eise with a mixture of 25 cm3 abs. Diethylamine with 100 em3 abs. Benzene added. It divides immediately. Diethylamine chlorohydrate. Turbination is carried out for a further 3/4 hours with exclusion of fire and then the precipitated diethylamine chlorohydrate is sucked off and washed with ether.
The combined ether-benzene solutions are shaken with 150 cm3 of saturated potassium bicarbonate solution, dried with sodium sulfate and evaporated to dryness. The oily residue is recrystallized from 350 a ?, petroleum ether 60/90 with the addition of charcoal.
16 g of the 3-methylester-5-diethyl amide pyridine-3,5-dicarboxylic acid melting at 47-48 are obtained. The new compound crystallizes in colorless, thin needles and dissolves easily in water and organic solvents, with the exception of petroleum ether, from which it can be easily recrystallized.
Claims (1)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH284073T | 1950-04-20 | ||
| CH306538T | 1950-04-25 | ||
| CH306559T | 1950-07-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH306538A true CH306538A (en) | 1955-04-15 |
Family
ID=27178154
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH306538D CH306538A (en) | 1950-04-20 | 1950-04-25 | Process for the preparation of a new pyridine-3,5-dicarboxylic acid derivative. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH306538A (en) |
-
1950
- 1950-04-25 CH CH306538D patent/CH306538A/en unknown
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