CH179320A - Process for the preparation of an indole series aldehyde. - Google Patents

Process for the preparation of an indole series aldehyde.

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Publication number
CH179320A
CH179320A CH179320DA CH179320A CH 179320 A CH179320 A CH 179320A CH 179320D A CH179320D A CH 179320DA CH 179320 A CH179320 A CH 179320A
Authority
CH
Switzerland
Prior art keywords
preparation
aldehyde
indole series
methylformylaniline
phenyl
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 CH179320A publication Critical patent/CH179320A/en

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  • Indole Compounds (AREA)

Description

  

  Verfahren zur Darstellung eines     Aldehyds    der     Indolreihe.            Uegenständ    des vorliegenden Zusatz  patentes ist ein Verfahren zur Darstellung  eines Aldehyds der     Indolreihe,    welches da  durch     gekennzeichnet.    ist, dass man     1-Methyl-          2-phenyl-6-nitroiridol,        Methylformylanilin    und  ein chlorhaltiges saures Kondensationsmittel  aufeinander einwirken lässt.

           Beispiel:       Zu 10,4 Gewichtsteilen     Methylformylani-          lin    werden 12,5 Gewichtsteile     Phosphorosy-          chlorid    gegeben, wobei unter Erwärmung  Reaktion eintritt. Nach zweistündigem Nach  rühren wird mit 40 Gewichtsteilen     o-Dichlor-          benzol    verdünnt und auf ca.     5110    abgekühlt.  Hierauf werden unter Rühren     portionsweise     19     Gewielitsteile        1-Methyl-2-pheriyl-6-nitro-          indol    in der Weise eingetragen, dass die  Temperatur nicht über 10   C steigt.

   Nach  ca. 15stündigem Stehenlassen bei gewöhn  licher Temperatur wird mit 200 Gewichts-    teilen Eis, dem 100 Gewichtsteile Natron  lauge 40 o     B6    zugesetzt sind, gut     ausgerührt,     die     Dichlorbenzollösung    im Scheidetrichter  getrennt und im Vakuum destilliert.

   Nach  dem zunächst das     o-Dichlorbenzol    und das  wiedergewonnene     Monomethylanilin        abdestil-          liert    sind, erhält man     1-Methyl-2-phenyl-6-          riitroindol-3-aldehyd    in einer Ausbeute von       85,3        %        der        Theorie.        Der        Aldehyd        schmilzt     bei<B>2330</B> C. Er soll zur Darstellung von  Farbstoffen Verwendung finden.



  Process for the preparation of an indole series aldehyde. The subject of the present additional patent is a process for the preparation of an aldehyde of the indole series, which is characterized by. is that 1-methyl-2-phenyl-6-nitroiridol, methylformylaniline and a chlorine-containing acidic condensation agent are allowed to interact.

           Example: 12.5 parts by weight of phosphorosyl chloride are added to 10.4 parts by weight of methylformylaniline, a reaction taking place when heated. After stirring for two hours, the mixture is diluted with 40 parts by weight of o-dichlorobenzene and cooled to approx. Then 19 parts by weight of 1-methyl-2-pheriyl-6-nitro-indole are added in portions with stirring in such a way that the temperature does not rise above 10.degree.

   After standing for about 15 hours at the usual temperature, 200 parts by weight of ice to which 100 parts by weight of sodium hydroxide solution 40 ° B6 have been added, stirred well, the dichlorobenzene solution separated in a separating funnel and distilled in vacuo.

   After the o-dichlorobenzene and the recovered monomethylaniline have first been distilled off, 1-methyl-2-phenyl-6-nitroindole-3-aldehyde is obtained in a yield of 85.3% of theory. The aldehyde melts at <B> 2330 </B> C. It is intended to be used to represent dyes.

Claims (1)

PATENTANSPRUCH: Verfahren zur Darstellung eines Aldehyds der Indolreihe, dadurch gekennzeichnet, dass man 1-Methyl-2-phenyl-6-nitroindol, Methyl- formylanilin und ein chlorhaltiges saures Kondensationsmittel aufeinander einwirken lässt. Der Aldehyd schmilzt bei 233 C. UNTERANSPUt1Cnt 1. Verfahren nach Patentanspruch, dadurch gekennzeichnet, dass man als Kondensa tionsmittel Phosphorogychlorid verwendet. 2. PATENT CLAIM: A process for the preparation of an aldehyde of the indole series, characterized in that 1-methyl-2-phenyl-6-nitroindole, methylformylaniline and a chlorine-containing acidic condensation agent are allowed to act on one another. The aldehyde melts at 233 ° C. UNTERANSPUt1Cnt 1. Process according to patent claim, characterized in that the condensation agent used is phosphorogychloride. 2. Verfahren nach Patentanspruch und Unter anspruch 1, dadurch gekennzeichnet, dass man das Metbylformylanilin zuerst auf Phosphorogychlorid zur Einwirkung bringt und auf das heaktionsprodukt das 1-DIe- thyl-2-phenyl-fi-nitroindol in Gegenwart von o-Dicblorbenzol bei einer Temperatur von etwa<B>5-100</B> C einwirken lässt. Process according to claim and sub-claim 1, characterized in that the methylformylaniline is first brought to action on phosphorogychloride and the 1-diethyl-2-phenyl-fi-nitroindole is applied to the reaction product in the presence of o-dicblobenzene at a temperature of about <B> 5-100 </B> C can act.
CH179320D 1933-05-13 1934-05-11 Process for the preparation of an indole series aldehyde. CH179320A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE179320X 1933-05-13
CH175349T 1934-05-11

Publications (1)

Publication Number Publication Date
CH179320A true CH179320A (en) 1935-08-31

Family

ID=25719655

Family Applications (1)

Application Number Title Priority Date Filing Date
CH179320D CH179320A (en) 1933-05-13 1934-05-11 Process for the preparation of an indole series aldehyde.

Country Status (1)

Country Link
CH (1) CH179320A (en)

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