CH230623A - Process for the production of indole-3-acetic acid. - Google Patents

Process for the production of indole-3-acetic acid.

Info

Publication number
CH230623A
CH230623A CH230623DA CH230623A CH 230623 A CH230623 A CH 230623A CH 230623D A CH230623D A CH 230623DA CH 230623 A CH230623 A CH 230623A
Authority
CH
Switzerland
Prior art keywords
indole
acetic acid
production
methylindole
saponified
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellsc Farbenindustrie
Original Assignee
Ig Farbenindustrie Ag
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 Ig Farbenindustrie Ag filed Critical Ig Farbenindustrie Ag
Publication of CH230623A publication Critical patent/CH230623A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18—Radicals substituted by 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)
  • Indole Compounds (AREA)

Description

  

      Verfahren    zur Herstellung von     Indol-3-essigsäure.       Gegenstand des Hauptpatentes ist ein  Verfahren zur     Herstellung    der     bekannten          Indol-3-Pssigsäure,    das dadurch gekennzeich  net ist, dass man     ein        3-Methylindol,    das an  der     Methylgruppe    eine tertiäre     Aminogruppe     enthält,

   mit     (#@ranwasserstoff        unter    Erwär  men und     in.    Anwesenheit eines Löse- oder  Verdünnungsmittels umsetzt     und    das so er  haltene     Indol-3-acetonitril    zur     Indol-3-essig-          säure    verseift.  



  Gegenstand des vorliegenden     Patentes    ist  nun ein Verfahren zur Herstellung der     Indol-          3-essigsäure,    das dadurch     gekennzeichnet    ist,  dass man ein     3-Methylindol,    das an der     Me-          thylgruppe    eine tertiäre     Aminogruppe    ent  hält, mit einem Salz des     Cyanwasserstoffes     bei erhöhter Temperatur in Anwesenheit  eines Löse- oder Verdünnungsmittels umsetzt  und das so erhaltene     Indol-3-acetonitril    zur       Indol-3-essigsäure    verseift.  



       Beispiel:     100 g     3-Dimethylaminomethyl-indol    wer  den mit 300 cm' Äthanol und einer Lösung  von 100g     Natriumcyanid    in 150     cm3    Wasser    einige Zeit im     Autoklaven    bei einer Bad  temperatur von 200  erhitzt. Die erhaltene  Lösung     wird    nun mit 200 cm' Wasser ver  setzt     und    das Äthanol mit Wasserdampf  abgeblasen. Die     wässrige    Lösung wird nach  dem Filtrieren mit verdünnter Schwefelsäure  bis zur kongosauren Reaktion angesäuert. Die  bekannte     Indol-3-essigsäure    fällt dabei in  farblosen Kristallen vom Schmelzpunkt 164  bis 165  aus.

   Die Ausbeute entspricht nahezu  der theoretisch     berechneten.  



      Process for the production of indole-3-acetic acid. The subject of the main patent is a process for the preparation of the known indole-3-passetic acid, which is characterized in that a 3-methylindole which contains a tertiary amino group on the methyl group is

   with (# @ ranhydrogen under heating and in the presence of a solvent or diluent, and the indole-3-acetonitrile obtained in this way is saponified to form indole-3-acetic acid.



  The present patent now relates to a process for the preparation of indole-3-acetic acid, which is characterized in that a 3-methylindole, which contains a tertiary amino group on the methyl group, is mixed with a salt of hydrogen cyanide at elevated temperature in Reacts the presence of a solvent or diluent and the indole-3-acetonitrile obtained in this way is saponified to give indole-3-acetic acid.



       Example: 100 g of 3-dimethylaminomethyl-indole are heated with 300 cm 'of ethanol and a solution of 100 g of sodium cyanide in 150 cm3 of water in the autoclave at a bath temperature of 200 for some time. The solution obtained is then ver with 200 cm 'of water and the ethanol is blown off with steam. After filtering, the aqueous solution is acidified with dilute sulfuric acid until it undergoes a Congo acid reaction. The well-known indole-3-acetic acid precipitates in colorless crystals with a melting point of 164 to 165.

   The yield almost corresponds to that calculated theoretically.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von Indol-3- essigsäure, dadurch gekennzeichnet, dass man ein 3-Methylindol, das an der Methylgruppe eine tertiäre Aminogruppe enthält, mit einem Salz des Cyanwasserstoffes bei erhöhter Tem peratur in Anwesenheit eines Löse- oder Ver dünnungsmittels umsetzt und das so erhal tene Indol-3-acetonitril zur Indol-3-essigsäure verseift. PATENT CLAIM: Process for the preparation of indole-3-acetic acid, characterized in that a 3-methylindole which contains a tertiary amino group on the methyl group is reacted with a salt of hydrogen cyanide at elevated temperature in the presence of a solvent or diluent and the indole-3-acetonitrile obtained in this way is saponified to give indole-3-acetic acid.
CH230623D 1939-05-27 1941-07-14 Process for the production of indole-3-acetic acid. CH230623A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE230623X 1939-05-27
CH225558T 1941-07-14

Publications (1)

Publication Number Publication Date
CH230623A true CH230623A (en) 1944-01-15

Family

ID=25726908

Family Applications (1)

Application Number Title Priority Date Filing Date
CH230623D CH230623A (en) 1939-05-27 1941-07-14 Process for the production of indole-3-acetic acid.

Country Status (1)

Country Link
CH (1) CH230623A (en)

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