CH309347A - Process for the preparation of 4-propylamino-salicylic acid. - Google Patents
Process for the preparation of 4-propylamino-salicylic acid.Info
- Publication number
- CH309347A CH309347A CH309347DA CH309347A CH 309347 A CH309347 A CH 309347A CH 309347D A CH309347D A CH 309347DA CH 309347 A CH309347 A CH 309347A
- Authority
- CH
- Switzerland
- Prior art keywords
- propylamino
- preparation
- salicylic acid
- acid
- aminophenol
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/52—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C229/54—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C229/64—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring the carbon skeleton being further substituted by singly-bound oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung von 4-Propylamino. salicylsäure.
4-Monoalkylamino-salicylsäuren und 4 Mono- (alkyloxyalkyl)-amino-salieylsäuren der allgemeinen Formel :
EMI1.1
in der R Alkyl-oder Alkyloxyalkylgruppen bedeuten, welche 2 oder mehr C-Atome in der am N-Atom gebundenen Alkylgruppe tragen, sind noeh nicht besehrieben worden.
Man kann zu diesen alkylierten bzw. alkyloxyalkylierten Aminosalicylsäuren gelangen, indem man. ein am N-Atom alkyliertes oder alkyloxyalkyliertes m-Amino-phenol, welches 2 oder mehr C-Atome in der am N-Atom gebundenen Alkylgruppe besitzt, mit Kohlensäure bei normaler oder erhöhter Temperatur und gegebenenfalls unter Anwendung von Druck in Gegenwart von Wasser und bzw. oder einem ändern Losungsmittel zur Umsetzung bringt.
An Stelle von Kohlensäure bzw. ausser Kohlensäure können auch Kohlendioxyd abspaltende Verbindungen, wie z. B. die Carbonate oder Bicarbonate der Alkalimetalle, verwendet werden. Zu dieser Umsetzung können an Stelle der freien, am N-Atom substituierten m-Aminophenole auch deren Alkaliverbindungen eingesetzt werden.
Die alkylierten bzw. alkyloxyalkylierten 4 Amino-salicylsäuren haben tuberkulostatische Eigenschaften. Sie dienen ferner zur Herstel- latig wertvoller Therapeutiea, wie z. B. Lokal- anästhetica.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung der 4-Propylamino-salieylsäure, welches dadurch gekennzeichnet ist, dass man N-propyl-m-amino-phenol mit Kohlensäure in Gegenwart eines Lösungs- mittels zur Umsetzung bringt. An Stelle des freien N-Propyl-m-amino-phenols kann man auch dessen Alkaliverbindungen zur Umsetzung bringen.
Beispiel :
30 g N-Propyl-m-amino-phenol werden mit 100g KHC03 in 50em3 60 /Oigem Alkohol unter Rühren in einem Autoklaven bei 120 bis 130 unter einem C02-Druck von 50 atü mehrere Stunden zur Peaktion gebracht. Man nimmt mit Wasser auf und isoliert nicht umgesetztes N-Propyl-m-amino-phenol durch Ausziehen mit Essigester. Beim Ansäuern der wässrigen Lösung bis zum pH-Wert von 4 fällt die 4-Propylamino-salieylsäure aus. Die anfallende 4-Propylamino-salicylsäure wird nach dem Trocknen aus Benzol und Essigester umkri- stallisiert ; Fp. 134 (Zersetzung).
Die Propylamino-salicylsäure soll f r thera peutische Zwecke, nämlich als Tuberkuloseheil- mittel, sowie zur Herstellung von Lokalanä- sthetica verwendet werden.
Process for the preparation of 4-propylamino. salicylic acid.
4-monoalkylamino-salicylic acids and 4 mono- (alkyloxyalkyl) -amino-salicylic acids of the general formula:
EMI1.1
in which R denotes alkyl or alkyloxyalkyl groups which have 2 or more carbon atoms in the alkyl group bonded to the N atom have not yet been described.
You can get to these alkylated or alkyloxyalkylated aminosalicylic acids by. an alkylated on the N atom or alkyloxyalkylated m-aminophenol, which has 2 or more carbon atoms in the alkyl group bonded to the N atom, with carbonic acid at normal or elevated temperature and optionally using pressure in the presence of water and or or a different solvent to implement.
Instead of carbonic acid or apart from carbonic acid, carbon dioxide-releasing compounds, such as. B. the carbonates or bicarbonates of the alkali metals can be used. For this reaction, instead of the free m-aminophenols substituted on the N atom, their alkali metal compounds can also be used.
The alkylated or alkyloxyalkylated 4 amino-salicylic acids have tuberculostatic properties. They are also used to manufacture valuable therapies, such as B. Local anesthetics.
The subject of the present patent is a process for the preparation of 4-propylamino-salicic acid, which is characterized in that N-propyl-m-aminophenol is reacted with carbonic acid in the presence of a solvent. Instead of the free N-propyl-m-aminophenol, it is also possible to react its alkali compounds.
Example:
30 g of N-propyl-m-aminophenol are reacted with 100 g of KHCO3 in 50em3 60% alcohol with stirring in an autoclave at 120 to 130 under a CO2 pressure of 50 atmospheres for several hours. It is taken up in water and unreacted N-propyl-m-aminophenol is isolated by extraction with ethyl acetate. When the aqueous solution is acidified to pH 4, the 4-propylamino-salicic acid precipitates. The resulting 4-propylaminosalicylic acid is recrystallized from benzene and ethyl acetate after drying; M.p. 134 (decomposition).
Propylaminosalicylic acid is said to be used for therapeutic purposes, namely as a tuberculosis remedy, as well as for the production of local anesthetics.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE309347X | 1951-08-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH309347A true CH309347A (en) | 1955-08-31 |
Family
ID=6121988
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH309347D CH309347A (en) | 1951-08-16 | 1952-07-24 | Process for the preparation of 4-propylamino-salicylic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH309347A (en) |
-
1952
- 1952-07-24 CH CH309347D patent/CH309347A/en unknown
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