CH217676A - Process for the preparation of N-ethyl-2-methylene-naphthoquinoline-w-aldehyde. - Google Patents

Process for the preparation of N-ethyl-2-methylene-naphthoquinoline-w-aldehyde.

Info

Publication number
CH217676A
CH217676A CH217676DA CH217676A CH 217676 A CH217676 A CH 217676A CH 217676D A CH217676D A CH 217676DA CH 217676 A CH217676 A CH 217676A
Authority
CH
Switzerland
Prior art keywords
aldehyde
methylene
ethyl
naphthoquinoline
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 CH217676A publication Critical patent/CH217676A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D221/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04—Ortho- or peri-condensed ring systems
    • C07D221/06—Ring systems of three rings
    • C07D221/10—Aza-phenanthrenes

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

  

      Verfahren    zur Herstellung von     N-Äthyl-2-methylen-naphthochinolin-m-aldehyd.       Zur Herstellung von     Methinf        arbstof    f en  eignen sieh die     oi-Ald@ehyde    der stickstoff  haltigen     heteroeyelischen    Basen.

   Es wurde  nun gefunden, dass man den     N-Äthyl-2-          methylen-naphtho-ehinolin-a)-a,Idehyd    folgen  der Konstitution  
EMI0001.0009     
    auf einfache Weise in guter Ausbeute erhält,  wenn man das     quartäre    Salz des     2-Methyl-          naphtho    -     chinolins    folgender     Zusammen-          setzung     
EMI0001.0016     
    zweckmässig in Gegenwart eines     organischen          Säureanhydrides,

      mit einem     Formamidin    der       allgemeinen    Formel  
EMI0001.0021     
         worin    R     Aryl    bedeutet, umsetzt und das  erhaltene Zwischenprodukt mit Alkalien  spaltet.  



  <I>Beispiel:</I>       1/10o        Mol        ss-Naphthochinaldin-jodäthylat     und     1/10o        Mol        (+    20% Überschuss)     Methyl-          diphenyl-formamidin    von folgender Formel  
EMI0001.0032     
    werden in 20 cm'     Ess.igsäureanhydrid    5 Mi  nuten gekocht, sodann wird' abgekühlt.

   Das  ausfallende gelbe Zwischenprodukt von der  Formel    
EMI0002.0001     
    wird abgesaugt, mit Alkohol und Äther ge  waschen und gegebenenfalls aus reichlich       b1ethanol    umkristallisiert.     1/""        111o1    dieses       Zwischenproduktes    wird in kochendem     lle-          thanal    gelöst, mit     1/"",        Mol        NaOH        (-i-    20  Überschuss) als 10%ige     wässrige    Lösung zer  setzt.

   Das     abgespaltene        Monomethylanilin     wird mit Wasserdampf     abde@stilliert.    Das       zurückbleibende        gelbbraune    Öl wird in  Benzol aufgenommen und mit Pottasche in  Gegenwart von Tierkohle getrocknet. Die  eingeengte     Benzollösung    wird mit Benzin  versetzt. Es fällt der     N-äthyl-2-nre.thylen-          naphtho-ehinolin-o)-aldehyd        a.ls    gelbes Pulver  vom Schmelzpunkt<B>1,58</B> bis 160     "    C aus.



      Process for the preparation of N-ethyl-2-methylene-naphthoquinoline-m-aldehyde. For the production of methine dyes, see the oi-Ald @ ehyde of nitrogen-containing heteroeyelic bases.

   It has now been found that the N-ethyl-2-methylene-naphtho-ehinolin-a) -a, idehyde follow the constitution
EMI0001.0009
    obtained in a simple manner in good yield if the quaternary salt of 2-methylnaphtho - quinoline of the following composition
EMI0001.0016
    expediently in the presence of an organic acid anhydride,

      with a formamidine of the general formula
EMI0001.0021
         wherein R is aryl, and the intermediate product obtained cleaves with alkalis.



  <I> Example: </I> 1 / 10o mol of ss-naphthoquinaldine iodoethylate and 1 / 10o mol (+ 20% excess) methyl-diphenyl-formamidine of the following formula
EMI0001.0032
    are boiled in 20 cm 'acetic anhydride for 5 minutes, then it is cooled.

   The precipitating yellow intermediate of the formula
EMI0002.0001
    is filtered off with suction, washed with alcohol and ether and, if necessary, recrystallized from plenty of ethanol. 1 / "" 111o1 of this intermediate product is dissolved in boiling methanol, and 1 / "", mol NaOH (-i 20 excess) is decomposed as a 10% aqueous solution.

   The split-off monomethylaniline is distilled off with steam. The yellow-brown oil that remains is taken up in benzene and dried with potash in the presence of animal charcoal. The concentrated benzene solution is mixed with gasoline. The N-ethyl-2-nre.thylen-naphtho-ehinolin-o) -aldehyde is precipitated as a yellow powder with a melting point of 1.58 to 160 ° C.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von N-tl.thyl- 2-methylen-naphtho-chinolin-cu-aldehyd, da durch gekennzeichnet, dass man Formamidine der allgemeinen Formel EMI0002.0028 worin R Arvl bedeutet, mit dein quaternären 2-3Ieithyl-rrapht,ho-chinolirr-äthylat folgender Konstitution EMI0002.0034 umsetzt und das erhaltene Zwischenprodukt einer alkalischen Spaltung unterwirft. PATENT CLAIM: A process for the production of N-tl.thyl- 2-methylene-naphtho-quinoline-cu-aldehyde, characterized in that one has formamidines of the general formula EMI0002.0028 where R Arvl means with your quaternary 2-3Ieithyl-rrapht, ho-quinolirr-ethylate of the following constitution EMI0002.0034 and the intermediate product obtained is subjected to alkaline cleavage. Die neue Verbindung ist ein gelbes Pulver vorn Schmelzpunkt 7_i8 bis 160') C. UNTERANSPRUCH: Verfahren gemäss Patentanspruch, da durch gekennzeichnet, dass die Umsetzung in Gegenwart esnes organischen Säureanhydri- des geschieht. The new compound is a yellow powder with a melting point of 7-18 to 160 ° C. SUBSTANTIAL CLAIM: Process according to patent claim, characterized in that the reaction takes place in the presence of organic acid anhydride.
CH217676D 1936-12-03 1937-10-26 Process for the preparation of N-ethyl-2-methylene-naphthoquinoline-w-aldehyde. CH217676A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE217676X 1936-12-03
DE217673X 1936-12-03

Publications (1)

Publication Number Publication Date
CH217676A true CH217676A (en) 1941-10-31

Family

ID=33098839

Family Applications (1)

Application Number Title Priority Date Filing Date
CH217676D CH217676A (en) 1936-12-03 1937-10-26 Process for the preparation of N-ethyl-2-methylene-naphthoquinoline-w-aldehyde.

Country Status (1)

Country Link
CH (1) CH217676A (en)

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