CH315082A - Process for the preparation of a new aldehyde derivative - Google Patents
Process for the preparation of a new aldehyde derivativeInfo
- Publication number
- CH315082A CH315082A CH315082DA CH315082A CH 315082 A CH315082 A CH 315082A CH 315082D A CH315082D A CH 315082DA CH 315082 A CH315082 A CH 315082A
- Authority
- CH
- Switzerland
- Prior art keywords
- aldehyde derivative
- dicarboxylic acid
- pyridine
- amide
- new
- 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
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung eines neuen Aldehydderivates Gegenstand des Patentes ist ein Verfah ren zur Herstellung eines neuen Aldehydderi- vates, welches gute keimtötende Eigensehaf- t.en besitzt. Die Verbindung und ha-Liptsäeh- lieh auch ihre löslichen Salze sollen zur Be-' kämpfung von Infektionskrankheiten verwen det -,verden.
Das den Gegenstand des Patentes bildende Verfahren ist dadurch gekennzeichnet, dass man auf Pyridin-3,4-dicarbonsäure-3-anid Fornialdeliy d einwirken, lässt, wobei sich das Pvi,idin-3,4-diearbonsäure-3-N-ozymethyl-amid bildet. Der Formaldehyd kann beispielsweise auch einer Formaldehyd liefernden Verbin dung, z. B. einem polymeren Formaldehyd (Ti-ioxymethylen., Paraformaldehyd), entstam men. Vorzugsweise wird die Umsetzung in alkalischem Milieu vorgenommen, da beim Ar beiten unter PH 7 leicht unerwünschte Neben produkte entstehen.
200 g Pyridin-3,4-dicarbonsäure-3-amid werden in 600 ein?, Wasser aufgeschlämmt und Unter Rühren verdünnte Natronlauge 1 :10 bis pH = 9 zugesetzt. Man erwärmt auf dem Wasserbad auf 80 und verrührt mit 450 cm3 36%iger wässeriger Formaldehydlösung, Man hält 15 Minuten bei 80 und stellt die )Vasser- stoffioneiAonzentration mit Hilfe von Natron lauge auf einen Wert von 9 bis 10 ein.
Da nach setzt man Aktivkohle zu, filtriert und neutralisiert mit Ameisensäure genau auf pH 7. Anschliessend rührt man Aceton ein, bis ein Niederschlag entsteht. Derselbe wird nach 24 Stunden abgesaugt und mit Aceton gewaschen. Durch Vakuumtrocknung bei 30 bis 40 erhält man das Natriumsalz des Pyri- din-3,4-dicarbonsäure-3-N-oxymethyl-amids als farbloses Pulver, das sich in kaltem Wasser bis zu 20% mit praktisch neutraler Reaktion löst.
Das so erhaltene Natriumsalz kann sehr leicht aus Wasser mit Hilfe von Aceton umge fällt werden. Die freie Verbindung kann durch vorsichtiges Ansäuern der wässerigen Lösung eines Salzes des Pyridin-3,4-dicarbonsäure-3- N-oxymethyl-amids erhalten werden. Sie stellt ein farbloses Pulver dar, das keinen scharfen Schmelzpunkt zeigt, sondern sich beim Er wärmen langsam zersetzt.
Die Salze der neuen Verbindung sind sehr beständig. Ihre wässerigen Lösungen reagie ren nahezu neutral und sind für Injektionen vorzüglich geeignet.
Die neue Verbindung lässt sich beispiels weise leicht in Form ihrer Salze, z. B. des Natriums, Kalziums, oder von Aminen, wie von Diäthylamin, Diäthanolamin, 1lorpholin usw" isolieren. Zu diesem Zwecke kann man, wie im Beispiel näher beschrieben, das dem ver wendeten alkalischen Kondensationsmittel ent sprechende Salz durch Vermischen der Reak- tionslösung mit einem organischen, mit Was ser mischbaren Lösungsmittel ausfällen.
Process for the production of a new aldehyde derivative The subject of the patent is a process for the production of a new aldehyde derivative which has good germicidal properties. The compound and its soluble salts are said to be used for combating infectious diseases.
The method forming the subject of the patent is characterized in that pyridine-3,4-dicarboxylic acid-3-anide Fornialdeliy d can act, whereby the Pvi, idine-3,4-dicarboxylic acid-3-N-ozymethyl- amide forms. The formaldehyde can, for example, a formaldehyde-supplying connec tion, z. B. a polymeric formaldehyde (Ti-ioxymethylene., Paraformaldehyde), entstam men. The reaction is preferably carried out in an alkaline medium, since undesirable by-products are easily formed when working below PH 7.
200 g of pyridine-3,4-dicarboxylic acid 3-amide are suspended in 600 ml of water and dilute sodium hydroxide solution 1:10 to pH = 9 is added with stirring. The mixture is heated to 80 on the water bath and stirred with 450 cm3 of 36% aqueous formaldehyde solution. The temperature is maintained at 80 for 15 minutes and the hydrogen ion concentration is adjusted to a value of 9 to 10 with the aid of sodium hydroxide solution.
Then activated charcoal is added, filtered and neutralized with formic acid to exactly pH 7. Then acetone is stirred in until a precipitate forms. The same is filtered off with suction after 24 hours and washed with acetone. Vacuum drying at 30 to 40 gives the sodium salt of pyridine-3,4-dicarboxylic acid 3-N-oxymethyl amide as a colorless powder which dissolves in cold water up to 20% with a practically neutral reaction.
The sodium salt thus obtained can very easily be turned over from water with the aid of acetone. The free compound can be obtained by carefully acidifying the aqueous solution of a salt of pyridine-3,4-dicarboxylic acid-3-N-oxymethyl-amide. It is a colorless powder that does not have a sharp melting point, but slowly decomposes when heated.
The salts of the new compound are very stable. Their aqueous solutions react almost neutrally and are ideally suited for injections.
The new compound can, for example, easily in the form of their salts, eg. B. of sodium, calcium, or amines, such as diethylamine, diethanolamine, 1lorpholine, etc. "For this purpose, as described in more detail in the example, the salt corresponding to the alkaline condensing agent used can be isolated by mixing the reaction solution with precipitate an organic solvent that is miscible with water.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH266516T | 1948-05-20 | ||
| CH315082T | 1953-04-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH315082A true CH315082A (en) | 1956-07-15 |
Family
ID=25730907
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH315082D CH315082A (en) | 1948-05-20 | 1953-04-25 | Process for the preparation of a new aldehyde derivative |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH315082A (en) |
-
1953
- 1953-04-25 CH CH315082D patent/CH315082A/en unknown
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