CH353742A - Process for preparing formyl-3-indoles - Google Patents

Process for preparing formyl-3-indoles

Info

Publication number
CH353742A
CH353742A CH353742DA CH353742A CH 353742 A CH353742 A CH 353742A CH 353742D A CH353742D A CH 353742DA CH 353742 A CH353742 A CH 353742A
Authority
CH
Switzerland
Prior art keywords
indoles
formyl
preparing
indole
dimethylformamide
Prior art date
Application number
Other languages
French (fr)
Inventor
Robert Wragg William
Stanley Fenton Anthony
Original Assignee
May & Baker Ltd
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 May & Baker Ltd filed Critical May & Baker Ltd
Publication of CH353742A publication Critical patent/CH353742A/en

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  • Indole Compounds (AREA)

Description

  

  Procédé de     préparation    de     formyl-3-indoles       La     présente    invention a pour objet un procédé  de préparation de nouveaux     formyl-3-indoles    de for  mule  
EMI0001.0005     
    dans laquelle R représente un     radical        aralcoyloxy.          Les    dérivés préférés sont ceux dans lesquels R est  un radical     benzyloxy,        fixé    de préférence en position 5.  



  Ces nouveaux composés sont des     intermédiaires     intéressants pour l'obtention de composés     thérapeuti-          quement    actifs.  



  Selon le procédé objet de la présente invention,  les nouveaux composés se préparent par réaction  d'un     indole        correspondant,    par exemple le     benzyl-          oxy-5-indole    (préparé comme décrit par BOEHME,       JACS,    75, 2502, 1953), avec une     formamide        dial-          coylée,    de     préférence    la     diméthylformamide,    en pré  sence d'un agent de     condensation,    de     préférence          l'oxychlorure    de phosphore, puis par hydrolyse,

   de       préférence    en milieu     alcalin,    du produit obtenu.  



  <I>Exemple</I>  66,8 g     d'oxychlorure    de phosphore sont ajoutés  goutte à goutte en agitant à 116g de     diméthyl-          formamide    dans un flacon protégé de l'humidité de  l'air à une température de 10 à 200. On ajoute alors  lentement en     agitant,    à 15-25, 98 g de benzyloxy-         5-indole    dans 69,5 g de     diméthylformamide.    Ensuite,  le mélange est chauffé à     35n    (  20) pendant 45 mi  nutes et versé sur de la glace pilée.

   On     filtre    le  solide qui se sépare, le lave à l'eau glacée et l'hydro  lyse par ébullition pendant deux minutes avec 550       cm3    de carbonate de sodium N. La suspension résul  tante est refroidie sur     glace    et le solide formé filtré,  lavé     successivement    avec 1750     cm3    d'eau,     200=3     de     méthanol    glacé et 750     cm3    d'éther.

   Après recris  tallisation dans un mélange de 400     cm3    de     diméthyl-          formamide    et 100     cm3    d'eau, on obtient le     benzyloxy-          5-formyl-3-indole    fondant à     239-241o.  



  Process for the preparation of formyl-3-indoles The present invention relates to a process for the preparation of novel formyl-3-indoles of the formula
EMI0001.0005
    in which R represents an aralkyloxy radical. The preferred derivatives are those in which R is a benzyloxy radical, preferably attached in position 5.



  These new compounds are useful intermediates for obtaining therapeutically active compounds.



  According to the process which is the subject of the present invention, the new compounds are prepared by reaction of a corresponding indole, for example benzyl-oxy-5-indole (prepared as described by BOEHME, JACS, 75, 2502, 1953), with a dialkylated formamide, preferably dimethylformamide, in the presence of a condensing agent, preferably phosphorus oxychloride, then by hydrolysis,

   preferably in an alkaline medium, of the product obtained.



  <I> Example </I> 66.8 g of phosphorus oxychloride are added dropwise with stirring to 116 g of dimethylformamide in a flask protected from air humidity at a temperature of 10 to 200. Then added slowly, with stirring, to 15-25, 98 g of benzyloxy-5-indole in 69.5 g of dimethylformamide. Then the mixture is heated at 35n (20) for 45 minutes and poured onto crushed ice.

   The solid which separates is filtered, washed with ice-cold water and hydrolysis by boiling for two minutes with 550 cm3 of N sodium carbonate. The resulting suspension is cooled on ice and the solid formed filtered off, washed successively. with 1750 cm3 of water, 200 = 3 of ice-cold methanol and 750 cm3 of ether.

   After recrystallization in a mixture of 400 cm3 of dimethylformamide and 100 cm3 of water, benzyloxy-5-formyl-3-indole is obtained, melting at 239-241o.

Claims (1)

REVENDICATION Procédé de préparation de formyl-3 indoles de formule EMI0001.0054 dans laquelle R représente un radical aralcoyloxy, caractérisé en ce que l'on fait réagir un indole cor respondant avec une formamide dialcoylée en pré sence d'un agent de condensation, puis en ce qu'on hydrolyse le produit obtenu. CLAIM Process for preparing 3-formylindoles of formula EMI0001.0054 in which R represents an aralkyloxy radical, characterized in that a corresponding indole is reacted with a dialkylated formamide in the presence of a condensing agent, then in that the product obtained is hydrolyzed.
CH353742D 1955-11-18 1956-11-19 Process for preparing formyl-3-indoles CH353742A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB353742X 1955-11-18

Publications (1)

Publication Number Publication Date
CH353742A true CH353742A (en) 1961-04-30

Family

ID=10377016

Family Applications (1)

Application Number Title Priority Date Filing Date
CH353742D CH353742A (en) 1955-11-18 1956-11-19 Process for preparing formyl-3-indoles

Country Status (1)

Country Link
CH (1) CH353742A (en)

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