DE614325C - Process for the introduction of aldehyde groups into indoles - Google Patents

Process for the introduction of aldehyde groups into indoles

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Publication number
DE614325C
DE614325C DEI47188D DEI0047188D DE614325C DE 614325 C DE614325 C DE 614325C DE I47188 D DEI47188 D DE I47188D DE I0047188 D DEI0047188 D DE I0047188D DE 614325 C DE614325 C DE 614325C
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DE
Germany
Prior art keywords
parts
weight
indoles
introduction
aldehyde groups
Prior art date
Legal status (The legal status 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 status listed.)
Expired
Application number
DEI47188D
Other languages
German (de)
Inventor
Dr Paul Wolff
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
IG Farbenindustrie AG
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
Priority to DEI47188D priority Critical patent/DE614325C/en
Application granted granted Critical
Publication of DE614325C publication Critical patent/DE614325C/en
Expired legal-status Critical Current

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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
    • C07D209/12—Radicals substituted by oxygen atoms

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Indole Compounds (AREA)

Description

Verfahren zur Einführung von Aldehydgruppen in Indole In dem Patent 514415 ist ein Verfahren zur Einführung von Aldehydgruppen in sauerstoffhaltige cyclische Verbindungen beschrieben. darin bestehend, daß man auf diese Verbindungen formylierte sekundäre Amine bei Gegenwart von chlorhaltigen sauren Kondensationsmitteln einwirken läßt.Method of introducing aldehyde groups into indoles In the patent 514415 is a method of introducing aldehyde groups into oxygen-containing cyclic compounds described. consisting in being able to access these connections formylated secondary amines in the presence of chlorine-containing acidic condensing agents can act.

Wie gefunden wurde, läßt sich dieses Verfahren nicht mir bei sauerstoffhaltigen Verbindungen anwenden, sondern man kann auf diese Weise' auch Aldeliydgruppen in in 2-Stellung arylierte oder alkylierte Indole mit freier .;=stellung, -wie z. B. i-llethyl-2-phenylindol, einführen. Die Aldehydgruppe tritt hierbei in den Pyrrolkern ein, und man erhält so z. B. den i - \lethyl-2-phenylindol-3-aldehyd. Damit sind Produkte auf. technisch einfache «'eise zugänglich geworden, die sehr wichtige Ausgangsstoffe für die Herstellung von I#'arl)stotfen bilden.As has been found, this procedure cannot be used with oxygen-containing Connections apply, but you can use this way 'also aldeliyd groups in in the 2-position arylated or alkylated indoles with free.; = position, -as z. B. i-llethyl-2-phenylindole. The aldehyde group enters the pyrrole nucleus a, and you get so z. B. the i - \ lethyl-2-phenylindol-3-aldehyde. So are Products on. technically simple «'have become accessible, the very important starting materials for the production of I # 'arl) stotfen form.

Beispiele i. Zu 2; Gewichtsteilen lIetlivlformylanilin werden 3o,6 Czewichtsteile Phosphoroxychlorid gegeben, wobei unter Erwärmung Reaktion eintritt. -Nach 2stündigem N achrühren -wird mit i5o Gewichtsteilen o-Dichlorbenzol verdünnt und auf etwa 5° abgekühlt. Hierauf werden unter Rühren portionsweise :11..1 Gewichtsteile i-\Ietliyl-=-phenylindol in der Weise eingetragen, daß die Temperatur nicht über i o:' steigt. Nach etwa i 5stündigem Stehenlassen bei gewöhnlicher Temperatur wird mit Zoo Gewichtsteilen Eis, dem ioo Gewichtsteile Natronlauge ¢o° B6 zugesetzt sind, gut ausgerührt, die Dichlorbenzollösung im Scheidetrichter getrennt und im Vakuum destilliert. Nachdem zunächst das o-Dichlorbenzol und das -wiedergewonnene Monomethylanilin abdestilliert sind, erhält man bei q. mm Druck und 229° den i-llethyl-2-phenylind0l-3-aldehyd in Ausbeute von 43,5 Gewichtsteilen = 92, 5 0%o der Theorie. Nach dem Umkristallisieren aus Ligroin zeigt der Aldehyd den Schmelzpunkt i28°. An Stelle von Phosphoröxychlorid können auch Thionylchlorid oder Sulfurchlorid genommen -werden.Examples i. To 2; Parts by weight of ethyl formylaniline are 3o, 6 Added parts by weight of phosphorus oxychloride, with reaction occurring with heating. After 2 hours of stirring, it is diluted with 150 parts by weight of o-dichlorobenzene and cooled to about 5 °. Then, in portions, with stirring: 11..1 parts by weight i- \ Ietliyl - = - phenylindole entered in such a way that the temperature does not exceed i o: 'increases. After standing for about 5 hours at ordinary temperature with zoo parts by weight of ice to which 100 parts by weight of caustic soda ¢ o ° B6 have been added, well stirred, the dichlorobenzene solution separated in a separating funnel and in vacuo distilled. After first the o-dichlorobenzene and the recovered monomethylaniline are distilled off, one obtains at q. mm pressure and 229 ° the i-llethyl-2-phenylind0l-3-aldehyde in a yield of 43.5 parts by weight = 92.5 0% o of theory. After recrystallization from ligroin, the aldehyde has a melting point of 128 °. Instead of phosphoroxychloride Thionyl chloride or sulfuric chloride can also be used.

2. 13,5 Gewichtsteile \IethylformylaniIin werden, wie in Beispiel i angegeben, finit 15,3 Gewichtsteilen Phosphoroxychlorid umgesetzt. Nach Verdünnen mit 5o Gewichtsteilen Chlorbenzol werden in gleicher Weise, wie beschrieben, 19,3 Gewichtsteile 2-Phenylindol in Reaktion gebracht und nach etwa 2o Stunden der entstandene 2-Phenylindol-3-aldehyd isoliert. Man erhält ihn in einer Ausbeute von 2o Gewichtsteilen = etwa 91 0'o der Theorie vom Schmelzpunkt 251°.2. 13.5 parts by weight of \ IethylformylaniIin are, as indicated in Example i, converted finitely 15.3 parts by weight of phosphorus oxychloride. After dilution with 50 parts by weight of chlorobenzene, 19.3 parts by weight of 2-phenylindole are reacted in the same manner as described and the 2-phenylindole-3-aldehyde formed is isolated after about 20 hours. It is obtained in a yield of 20 parts by weight = about 910 ° of theory with a melting point of 251 °.

3. Bei gleicher Ausführung, -wie in Beispiel i angegeben, und Anwendtnig folgender Ansatzmengen: io,.l Gewichtsteile Methyl- formylanilin, 12..5 Gewichtsteile Phosphoroxy- chlorid, .1o Gewichtsteile o-Dichlorbenzol er- hält man aus i cg Gerichtsteilen r-1lethyl- 2-phenyl-6-nitroindol 18 Gewichtsteile i-1lethvl- 2-phenyl-6-iiitroindol-3-aldehyd vom Schmelz- punkt a33°. - 5;,3 0 o der Theorie. Aus 1.1 Gewichtsteilen i # a-Dimethylindol erhält man bei Anwendung von 13,5 Ge- ivichtsteilen 2#Iethylformylanilin und 15,3 Ge- wichtsteilen Phosphoroxvchlorid in 5o,o Ge- wichtsteilen o-Dichlorbenzol als Lösungs- mittel, wenn man die Operation in der Luster Beispirl i angegebenen Weise ausführt, 13,5 Gewichtsteile i # 2-Ditilethylindol-iä-aldehyd vom Schmelzpunkt 132' = etwa S i t, o der Theorie. 3. With the same design, as specified in example i, and the following applies Mixture quantities: io, .l parts by weight of methyl formylaniline, 12..5 parts by weight phosphoroxy chloride, .1o parts by weight of o-dichlorobenzene one keeps from i cg parts of the dish r-1lethyl- 2-phenyl-6-nitroindole 18 parts by weight i-1lethvl- 2-phenyl-6-nitroindole-3-aldehyde from the melt point a33 °. - 5;, 3 0 o of theory. From 1.1 parts by weight of i # a-dimethylindole obtained with the application of 13.5 iv not share 2 # ethylformylaniline and 15.3 parts by weight of phosphorus oxychloride in 5o, o parts by weight of o-dichlorobenzene as a solution medium if you have the operation in the chandelier Example in the manner indicated, 1 3.5 parts by weight of i # 2-ditilethylindol-iä-aldehyde from melting point 132 ' = about S it, o der Theory.

Claims (1)

PATENT.UN SPRUCH
Verfahren zur Einführung von aldehyd- gruppen in Indole, dadurch gekennzeich- net, daß man auf in 2-Stellung arylierte oder all:ylierte Indole mit freier 3-Stellung lfethvlformvlanilin in Gegenwart von chlorhaltigen sauren Kondensationsmitteln und von Verdünnwigsmitteln einwirken läßt.
PATENT.UN APPLICATION
Process for the introduction of aldehyde groups in indoles, characterized by net that one arylated on in the 2-position or all: ylated indoles with a free 3-position lfethvlformvlanilin in the presence of acidic condensing agents containing chlorine and act of thinners leaves.
DEI47188D 1933-05-14 1933-05-14 Process for the introduction of aldehyde groups into indoles Expired DE614325C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEI47188D DE614325C (en) 1933-05-14 1933-05-14 Process for the introduction of aldehyde groups into indoles

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEI47188D DE614325C (en) 1933-05-14 1933-05-14 Process for the introduction of aldehyde groups into indoles

Publications (1)

Publication Number Publication Date
DE614325C true DE614325C (en) 1935-06-06

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Family Applications (1)

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DEI47188D Expired DE614325C (en) 1933-05-14 1933-05-14 Process for the introduction of aldehyde groups into indoles

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DE (1) DE614325C (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3042684A (en) * 1962-07-03 J-ethtl-jj-nitrovinylindole
US3055912A (en) * 1957-11-11 1962-09-25 Ciba Geigy Corp New substituted indole-(2)-aldehydes and process for their manufacture

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3042684A (en) * 1962-07-03 J-ethtl-jj-nitrovinylindole
US3055912A (en) * 1957-11-11 1962-09-25 Ciba Geigy Corp New substituted indole-(2)-aldehydes and process for their manufacture

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