CH139805A - Process for the preparation of an amide of a heterocyclic carboxylic acid. - Google Patents
Process for the preparation of an amide of a heterocyclic carboxylic acid.Info
- Publication number
- CH139805A CH139805A CH139805DA CH139805A CH 139805 A CH139805 A CH 139805A CH 139805D A CH139805D A CH 139805DA CH 139805 A CH139805 A CH 139805A
- Authority
- CH
- Switzerland
- Prior art keywords
- preparation
- hydrogenation
- carboxylic acid
- amide
- carried out
- Prior art date
Links
Classifications
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Darstellung eines Armdes einer heterozyklisehen Carbonsäure. Es wurde gefunclens dass man zu einem Amid einer heterozylD,lischen Carbonsäure gelangen kann, indem man den NTicotyl-p- aminobenzoesäureäthylester hydriert. Als Hydrierungsmittel sind zum Beispiel Wasser stoff in Gegenwart katalytisch wirkender Metalle oder Metallgemische, Alkalimetalle in Gegenwart eines Alkohols oder Metalle und Säuren zu nennen.
Der Nipecotyl-p-aminobenzoesäureäthyl- ester .stellt ein weisses Kristallpulver vom Schmelzpunkt 160,5 dar. das in den meisten organischen Lösungsmitteln löslich ist. Mit Säuren werden leicht lösliche, neutrale Salze erhalten.
Die neue Verbindung kann entweder selbst therapeutische Verwendung finden oder als Zwischenprodukt zur Herstellung pharma zeutischer Verbindungen dienen.
BeisjxM: 59 Teile I\Ticotyl-p-aminobenzoesä.ureäthyl- esi:er (erhalten aus \ilzotinsäurechlorid und p-Aminobenzoesäureäthylester bei Gegenwart von Pyridin; filzige Nädelchen vom Schmelz punkt<B>117</B> ) werden mit 250 Teilen Dekalin und 15 Teilen Nickelkataly sator unter 10 bis 40 Atmosphären Wasserstoffdruck auf 150 bis 165 erhitzt.
Nach Beendigung der Wasserstoffaufnahme wird das Dekalin, das keine Substanz enthält, abgegossen, das zu rückbleibende zähe Harz in heissem Aceton gelöst und die Lösung vom Katalysator ab filtriert. Beim Stehen scheidet sich der Ni pecotyl-p-aminabenzoesäureester in schönen Kristallen aus.
Die Hydrierung gelingt in gleicher Weise, zum Beispiel bei Anwendung von Natrium und Alkohol oder von Zink in Gegenwart einer Säure.
Method for preparing an arm of a heterocyclic carboxylic acid. It has been found that an amide of a heterocyclic carboxylic acid can be obtained by hydrogenating the ethyl Nicotyl-p-aminobenzoate. Hydrogen in the presence of catalytically active metals or metal mixtures, alkali metals in the presence of an alcohol or metals and acids may be mentioned as hydrogenating agents.
The ethyl nipecotyl-p-aminobenzoate is a white crystal powder with a melting point of 160.5 which is soluble in most organic solvents. Easily soluble, neutral salts are obtained with acids.
The new compound can either find therapeutic use itself or serve as an intermediate for the preparation of pharmaceutical compounds.
For example: 59 parts of ticotyl-p-aminobenzoesä.ureäthyl- esi: er (obtained from \ ilzotinic acid chloride and p-aminobenzoic acid ethyl ester in the presence of pyridine; felty needles with a melting point <B> 117 </B>) are mixed with 250 parts of decalin and 15 parts of nickel catalyst heated to 150 to 165 under 10 to 40 atmospheres of hydrogen pressure.
After the uptake of hydrogen has ended, the decalin, which does not contain any substance, is poured off, the viscous resin that remains is dissolved in hot acetone and the solution is filtered off from the catalyst. When standing, the Ni pecotyl-p-aminabenzoic acid ester separates out in beautiful crystals.
The hydrogenation succeeds in the same way, for example when using sodium and alcohol or zinc in the presence of an acid.
Claims (1)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH139805T | 1928-07-24 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH139805A true CH139805A (en) | 1930-05-15 |
Family
ID=4396918
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH139805D CH139805A (en) | 1928-07-24 | 1928-07-24 | Process for the preparation of an amide of a heterocyclic carboxylic acid. |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH139805A (en) |
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1928
- 1928-07-24 CH CH139805D patent/CH139805A/en unknown
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