CH236162A - Process for the preparation of 2-methyl-3-carbäthoxyamino-4-phenoxymethyl-5-cyano-6-chloropyridine. - Google Patents
Process for the preparation of 2-methyl-3-carbäthoxyamino-4-phenoxymethyl-5-cyano-6-chloropyridine.Info
- Publication number
- CH236162A CH236162A CH236162DA CH236162A CH 236162 A CH236162 A CH 236162A CH 236162D A CH236162D A CH 236162DA CH 236162 A CH236162 A CH 236162A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- cyano
- methyl
- phenoxymethyl
- carbäthoxyamino
- 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
- C07D213/84—Nitriles
- C07D213/85—Nitriles in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Description
Verfahren zur Darstellung von 2-)lethyl-3-carbäthoxyamino-4-phenoxymethyl- 5-eyano-6-chlor -pyridin. 2 - Methyl -3- carbäthoxyamino-4-phenoxy- znethyl - 5 - cyano- 6 - chlor - pyridin wird nach dem Hauptpatent aus 2-Methyl-4-phenoxy methyl-5-cyano-6-chlorpyridin-3-carbonsäure- hydrazid dadurch gewonnen, dass diese Ver bindung in das Bäureazid übergeführt und das Säureazid mit Alkoholen verkocht wird.
Die Ausgangsverbindung kann man aus 2- Methyl - 4 - phenoxymethyl - 5 - cyano -6-chlor- pyridin-carbonsäurechlorid dadurch erhalten. dass man diese Verbindung in Gegenwart von freien Alkalien mit Hydrazin umsetzt.
Es wurde nun gefunden, dass man 2-Me- thyl - 3- carbäthoxyamino-4-phenoxymethyl-5- cyano-6-chlor-pyridin aus 2-Methyl-4-phen- oxymethyl-5-cyano-6-chlor,- pyridin-3-carbon- säurechlorid auf einfacherem Wege und in wesentlich besserer Ausbeute dadurch her stellen kann,
dass man die genannte Verbin dung mit einem Salz der Stickstoffv>asser- stoffsäure unmittelbar in das Säureazid über führt und dieses dann mit Alkohol verkocht. Durch die Ausschaltung des Umweges über das Säurehydrazid können erhebliche Sub stanzverluste vermieden werden.
Das 2-Methyl-3-carbäthoxyamino-4-phen- oxymethyl-5-cyano-6-chlor-pyridin bildet ein Zwischenprodukt für die Herstellung von Arzneimitteln.
<I>Beispiel:</I> In 100 Raumteilen Dioxan werden 16 Ge wichtsteile 2 - Methyl - 4 - phenoxymethyl - 5 - cyano <B>-16</B> --chlor-pyridin-3 - carbonsäurechlorid unter Rühren aufgelöst. Nach Abkühlung der Lösung auf etwa 5 wird sie in eine Lösung von 5 Teilen Natriumazid in 25 Teilen Was ser eingegossen. Bald setzt eine Ausfällung des Azids ein, welche nach etwa 11/2 Stunden beendigt ist.
Nach Zugabe reichlicher Mengen Wasser, welches die Azidabscheidung beför dert, kann das Azid abfiltriert werden.
Das Azid wird nun nach und nach in etwa 65 warmem Alkohol (etwa 30 Raumteile) eingetragen. Unter starker Stickstoffentwick lung entsteht eine klare Lösung. Nach Zusatz von Wasser (etwa 30 Teile) kristallisiert
EMI0002.0001
beim <SEP> Stehen <SEP> 2-.L#Iethyl-3-ca.rbäthoxyainino-4 phenoxymethyl-ä-cyano-6-chlor-pyridin <SEP> vom
<tb> Schmelzpunkt <SEP> 167 <SEP> aus.
Process for the preparation of 2-) ethyl-3-carbäthoxyamino-4-phenoxymethyl-5-eyano-6-chloro-pyridine. According to the main patent, 2-methyl -3-carbäthoxyamino-4-phenoxy-znethyl-5-cyano-6-chloro-pyridine is hydrazide from 2-methyl-4-phenoxy-methyl-5-cyano-6-chloropyridine-3-carboxylic acid obtained by converting this compound into the acid azide and boiling the acid azide with alcohols.
The starting compound can be obtained from 2-methyl-4-phenoxymethyl-5-cyano-6-chloro-pyridine-carboxylic acid chloride. that this compound is reacted with hydrazine in the presence of free alkalis.
It has now been found that 2-methyl-3-carbäthoxyamino-4-phenoxymethyl-5-cyano-6-chloropyridine can be obtained from 2-methyl-4-phenoxymethyl-5-cyano-6-chlorine, pyridine-3-carboxylic acid chloride can thereby be produced in a simpler way and in significantly better yield,
that the compound mentioned is converted directly into the acid azide with a salt of nitrogenous hydrogen acid and this is then boiled with alcohol. By eliminating the detour via the acid hydrazide, considerable substance losses can be avoided.
The 2-methyl-3-carbäthoxyamino-4-phenoxymethyl-5-cyano-6-chloropyridine forms an intermediate product for the manufacture of drugs.
<I> Example: </I> 16 parts by weight of 2 - methyl - 4 - phenoxymethyl - 5 - cyano <B> -16 </B> - chloropyridine-3 - carboxylic acid chloride are dissolved in 100 parts by volume of dioxane while stirring. After cooling the solution to about 5, it is poured into a solution of 5 parts of sodium azide in 25 parts of water. Precipitation of the azide soon sets in, which is complete after about one and a half hours.
After adding copious amounts of water, which promotes the azide separation, the azide can be filtered off.
The azide is now gradually added to about 65 warm alcohol (about 30 parts by volume). A clear solution is formed with strong nitrogen development. After adding water (about 30 parts) crystallizes
EMI0002.0001
when <SEP> standing <SEP> 2-.L # Ethyl-3-ca.rbäthoxyainino-4 phenoxymethyl-a-cyano-6-chloropyridine <SEP> from
<tb> Melting point <SEP> 167 <SEP>.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH217229T | 1940-09-10 | ||
| CH236162T | 1942-02-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH236162A true CH236162A (en) | 1945-01-15 |
Family
ID=25725918
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH236162D CH236162A (en) | 1940-09-10 | 1942-02-20 | Process for the preparation of 2-methyl-3-carbäthoxyamino-4-phenoxymethyl-5-cyano-6-chloropyridine. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH236162A (en) |
-
1942
- 1942-02-20 CH CH236162D patent/CH236162A/en unknown
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