CH214788A - Process for the preparation of N-methyl-3,3-dimethylindolenine-2-methylene-w-aldehyde. - Google Patents

Process for the preparation of N-methyl-3,3-dimethylindolenine-2-methylene-w-aldehyde.

Info

Publication number
CH214788A
CH214788A CH214788DA CH214788A CH 214788 A CH214788 A CH 214788A CH 214788D A CH214788D A CH 214788DA CH 214788 A CH214788 A CH 214788A
Authority
CH
Switzerland
Prior art keywords
aldehyde
methyl
dimethylindolenine
methylene
preparation
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 CH214788A publication Critical patent/CH214788A/en

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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 Herstellung von     N-methyl-3,3-dimethylindolenin-2-methylen-w-aldehyd.       Zur Herstellung von     Methinfarbstoffen     eignen sich die     co-Aldehyde    der stickstoff  haltigen     heterocyclischen    Basen.

   Es     wurde          gefunden,    dass man den     N-methyl-3,3-dime-          thylindolenin-2-methylen-co-aldehyd    folgen  der Konstitution:  
EMI0001.0010     
    auf einfache Weise in guter Ausbeute erhält,  wenn man das     quartäre    Salz des     2,3,3-Tri-          methylindolenins    folgender Zusammenset  zung:  
EMI0001.0014     
    zweckmässig in Gegenwart eines organischen       Säureanhydrids,    mit einem     Formamidin    der       allgemeinen    Formel:

    
EMI0001.0018     
    worin R     Aryl    bedeutet, umsetzt und das er  haltene     Zwischenprodukt    mit Alkalien spal  tet. Für die Umsetzung geeignete Formami  dine sind beispielsweise:       N-methyl        diphenyl-f        ormamidine,          N-benzyldiphenyl-formamidine,          N-p-tolyldiphenyl-formamidine.     Die     Formamidine    erhält man zum Bei  spiel durch Umsetzen der     Formylverbindung     eines primären aromatischen Amins mit  sekundären aromatischen Stickstoffverbin  dungen, in     Anwesenheit    von Phosphor  chloriden.

        <I>Beispiel:</I>  102 Teile     2,3,3-TrimethylindöIeninbrom-          methylat,    95 Teile     2-Methylindolinylphenyl-          formamidin    (Siedepunkt<B>191'</B> bei 3 mm  Druck, hergestellt aus     Formanilid        und        2-          Methylindolin    in     Anwesenheit    von     Phosphor-          trichlorid)    und 100 Teile     Essigsäureanhy-          drid    erhitzt man 2     Stunden    lang am Rück  flusskühler zum Sieden.

   Die Umsetzungsmasse  wird in 300     Teile    Wasser gegossen und warm  mit Natronlauge bis zur alkalischen Reak  tion versetzt. Das alkalische Gemisch wird       einer        Wasserdampfdestillation    unterworfen,  bis keine Öle mehr übergehen. Der     Rückstand     wird mit Benzol aufgenommen,     bis    zur neu  tralen Reaktion gewaschen, mit wasserfreiem       Natriumcarbonat    getrocknet und nach dem       Abdestillieren    des Benzols im Vakuum frak  tioniert     destilliert.    Der entstandene 1,3,3  Trimethyl-2-methylenindolin-m-aldehyd sie  det unter 2 mm     Druck    bei 170 bis 172  .

   Er  bildet nach dem     Umlösen    aus Benzol Kri  stalle vom Schmelzpunkt 117 bis<B>118'.</B>



      Process for the preparation of N-methyl-3,3-dimethylindolenine-2-methylene-w-aldehyde. The co-aldehydes of the nitrogen-containing heterocyclic bases are suitable for the production of methine dyes.

   It was found that the N-methyl-3,3-dimethylindolenine-2-methylene-co-aldehyde follow the constitution:
EMI0001.0010
    obtained in a simple manner in good yield if the quaternary salt of 2,3,3-trimethylindolenine is obtained as follows:
EMI0001.0014
    conveniently in the presence of an organic acid anhydride, with a formamidine of the general formula:

    
EMI0001.0018
    wherein R is aryl, reacts and the intermediate he obtained is splitted with alkalis. Formamides suitable for the reaction are, for example: N-methyl diphenyl-formamidines, N-benzyldiphenylformamidines, N-p-tolyldiphenylformamidines. The formamidines are obtained, for example, by reacting the formyl compound of a primary aromatic amine with secondary aromatic nitrogen compounds in the presence of phosphorus chlorides.

        <I> Example: </I> 102 parts of 2,3,3-trimethylindolene bromomethylate, 95 parts of 2-methylindolinylphenylformamidine (boiling point <B> 191 '</B> at 3 mm pressure, made from formanilide and 2- Methylindoline in the presence of phosphorus trichloride) and 100 parts of acetic anhydride are heated to boiling for 2 hours on a reflux condenser.

   The reaction mass is poured into 300 parts of water and warm sodium hydroxide solution is added until it is alkaline. The alkaline mixture is subjected to steam distillation until no more oils pass over. The residue is taken up with benzene, washed until neutral reaction, dried with anhydrous sodium carbonate and, after the benzene has been distilled off, fractionally distilled in vacuo. The 1,3,3 trimethyl-2-methylene-indoline-m-aldehyde formed under 2 mm pressure at 170 to 172.

   After dissolving from benzene, it forms crystals with a melting point of 117 to <B> 118 '. </B>

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von N-methyl- 3,3-dimethylindolenin-2-methylen-m-aldehyd, dadurch gekennzeichnet, dass man ein Form- amidin der allgemeinen Formel EMI0002.0030 worin R Aryl bedeutet, mit dem quartären 2,3,3-Trimethylindolenin der Formel EMI0002.0034 umsetzt und das erhaltene Zwischenprodukt einer alkalischen Spaltung unterwirft. Die neue Verbindung siedet unter 2 mm Druck bei 170 bis 172 . PATENT CLAIM: Process for the preparation of N-methyl-3,3-dimethylindolenine-2-methylen-m-aldehyde, characterized in that a formamide of the general formula EMI0002.0030 wherein R is aryl, with the quaternary 2,3,3-trimethylindolenine of the formula EMI0002.0034 reacts and the intermediate product obtained is subjected to alkaline cleavage. The new compound boils under 2mm pressure at 170 to 172. UNTERANSPRUCH: Verfahren gemäss Patentanspruch, da durch gekennzeichnet, dass die Umsetzung in Gegenwart eines organischen Säureanhydrids geschieht. SUBCLAIM: Process according to claim, characterized in that the reaction takes place in the presence of an organic acid anhydride.
CH214788D 1936-12-03 1937-10-26 Process for the preparation of N-methyl-3,3-dimethylindolenine-2-methylene-w-aldehyde. CH214788A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE214788X 1936-12-03
DE217673X 1936-12-03

Publications (1)

Publication Number Publication Date
CH214788A true CH214788A (en) 1941-05-15

Family

ID=33098835

Family Applications (1)

Application Number Title Priority Date Filing Date
CH214788D CH214788A (en) 1936-12-03 1937-10-26 Process for the preparation of N-methyl-3,3-dimethylindolenine-2-methylene-w-aldehyde.

Country Status (1)

Country Link
CH (1) CH214788A (en)

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