CH148957A - Process for the preparation of a basic ether of the pyridine series. - Google Patents

Process for the preparation of a basic ether of the pyridine series.

Info

Publication number
CH148957A
CH148957A CH148957DA CH148957A CH 148957 A CH148957 A CH 148957A CH 148957D A CH148957D A CH 148957DA CH 148957 A CH148957 A CH 148957A
Authority
CH
Switzerland
Prior art keywords
sep
preparation
pyridine series
carboxylic acid
basic ether
Prior art date
Application number
Other languages
German (de)
Inventor
Gesellschaft Fuer Chemis Basel
Original Assignee
Chem Ind Basel
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Chem Ind Basel filed Critical Chem Ind Basel
Publication of CH148957A publication Critical patent/CH148957A/en

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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 Darstellung eines     basischen    Äthers der     Pyridinreihe.       Es wurde gefunden, dass man zu einem  basischen Äther der     Pyridinreihe    gelangen  kann, wenn man     Diäthylamino-äthanol    auf       2-Halogenpy        -idin-3-carbonsäure-N-äthylanilid     in Gegenwart säurebindender Mittel einwir  ken lässt.  



  Das entstandene     2-Diätbylamirioätboxy-          pyridiii-3-carborisäiire-N-äthylanilid    bildet ein  gelbes 01. Es ist in Wasser schwer, in or  ganischen Lösungsmitteln und in Säuren leicht  löslich. Das farblose     Monochlorhydrat    der  Base schmilzt bei 142  .  



  Die neue Base soll als solche oder als  Zwischenprodukt für     therapeutische    Zwecke  Verwendung finden.  



  <I>Beispiel:</I>  . Eine Lösung von 2,8 Teilen Natrium in  überschüssigem     Diäthylaminoäthanol    wird  mit 25,8 Teilen     2-Chlorpyridin-3-carbonsäure-          N-äthylanilid    versetzt und     iin    Ölbad erwärmt.  Nach beendigter Reaktion wird der über  schüssige     Aminoalkohol        abdestilliert    und die  
EMI0001.0017     
  
    neue <SEP> Base <SEP> durch <SEP> Aufnahme <SEP> in <SEP> Äther <SEP> und
<tb>  Vertreibung <SEP> des <SEP> Lösungsmittels <SEP> isoliert. <SEP> Durch
<tb>  Kristallisation <SEP> aus <SEP> Essigätliei- <SEP> und <SEP> Alkohol
<tb>  bekommt <SEP> man <SEP> das <SEP> Chlorhydrat <SEP> in <SEP> reiner <SEP> Form.
<tb>  



  Das <SEP> 2-Chlorpyridiii-3-carbonsäure-1\T-ätliyl  anilid <SEP> vom <SEP> Schmelzpunkt <SEP> 119-120 <SEP>   <SEP> erhält
<tb>  man <SEP> durch <SEP> Umsetzen <SEP> von <SEP> N-Ätliylauiliii <SEP> finit
<tb>  2-Chlorpyridin-3-carborisäurechlorid.
<tb>  



  An <SEP> Stelle <SEP> von <SEP> 2-Chlorp3-ridin-3-cai-bon  säiire-N-äthylaiiilid <SEP> können <SEP> auch <SEP> andere <SEP> 2  Halogenpyridiri-3-carbonsäure-N <SEP> -äthylaiiilide
<tb>  Verwendung <SEP> finden.



  Process for the preparation of a basic ether of the pyridine series. It has been found that a basic ether of the pyridine series can be obtained if diethylamino-ethanol is allowed to act on 2-halopyidine-3-carboxylic acid-N-ethylanilide in the presence of acid-binding agents.



  The resulting 2-dietbylamirioätboxy- pyridiii-3-carborisäiire-N-ethylanilide forms a yellow 01. It is difficult in water, easily soluble in organic solvents and in acids. The colorless monochlorohydrate of the base melts at 142.



  The new base is intended to be used as such or as an intermediate for therapeutic purposes.



  <I> Example: </I>. A solution of 2.8 parts of sodium in excess diethylaminoethanol is mixed with 25.8 parts of 2-chloropyridine-3-carboxylic acid-N-ethylanilide and heated in an oil bath. After the reaction has ended, the excess amino alcohol is distilled off and the
EMI0001.0017
  
    new <SEP> base <SEP> by <SEP> recording <SEP> in <SEP> ether <SEP> and
<tb> expulsion <SEP> of the <SEP> solvent <SEP> isolated. <SEP> through
<tb> Crystallization <SEP> from <SEP> acetic acid <SEP> and <SEP> alcohol
<tb> <SEP> you get <SEP> the <SEP> hydrochloride <SEP> in <SEP> pure <SEP> form.
<tb>



  The <SEP> 2-chloropyridiii-3-carboxylic acid-1 \ T-ätliyl anilid <SEP> has a melting point <SEP> 119-120 <SEP> <SEP>
<tb> man <SEP> by <SEP> converting <SEP> from <SEP> N-Ätliylauiliii <SEP> finite
<tb> 2-chloropyridine-3-carboric acid chloride.
<tb>



  Instead of <SEP> <SEP> of <SEP> 2-chlorop3-ridin-3-cai-bon säiire-N-ethylaiiilid <SEP>, <SEP> can also use <SEP> other <SEP> 2 halopyridiri-3-carboxylic acid N <SEP> -äthylaiiilide
<tb> Find use <SEP>.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eine, basischen Äthers der Pyridinreihe, dadurch gekeiiri- zeichnet, dass man Diäthylaminoäthanol auf 2-Halogenpyridiri-3-carbonsäure-N- äthylanilid in Gegenwart säurebindender Mittel einwir ken lässt. Das entstandene 2-Diäthylaminoäthox@-- pyridin-3-carbonsäure-N-äthylanilid bildet ein gelbes 01. Es ist in Wasser schwer, in organischen Lösungsmitteln und in Säuren leicht löslich. Das farblose 1Monochlorhydrat der Base schmilzt bei 1420. PATENT CLAIM: Process for the preparation of a basic ether of the pyridine series, characterized in that diethylaminoethanol is allowed to act on 2-halopyridiric-3-carboxylic acid-N-ethylanilide in the presence of acid-binding agents. The resulting 2-diethylaminoethox @ - pyridine-3-carboxylic acid-N-ethylanilide forms a yellow 01. It is difficult in water and easily soluble in organic solvents and acids. The colorless monochlorohydrate of the base melts at 1420. Die neue Base soll als solche oder als Zwischenprodukt für therapeutische Zwecke Verwendung finden. The new base is intended to be used as such or as an intermediate for therapeutic purposes.
CH148957D 1929-08-10 1929-08-10 Process for the preparation of a basic ether of the pyridine series. CH148957A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH146546T 1929-08-10
CH148957T 1929-08-10

Publications (1)

Publication Number Publication Date
CH148957A true CH148957A (en) 1931-08-15

Family

ID=25714870

Family Applications (1)

Application Number Title Priority Date Filing Date
CH148957D CH148957A (en) 1929-08-10 1929-08-10 Process for the preparation of a basic ether of the pyridine series.

Country Status (1)

Country Link
CH (1) CH148957A (en)

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