CH302907A - Process for the preparation of 1-amino-3-imino-methylisoindolenine. - Google Patents

Process for the preparation of 1-amino-3-imino-methylisoindolenine.

Info

Publication number
CH302907A
CH302907A CH302907DA CH302907A CH 302907 A CH302907 A CH 302907A CH 302907D A CH302907D A CH 302907DA CH 302907 A CH302907 A CH 302907A
Authority
CH
Switzerland
Prior art keywords
amino
imino
methylisoindolenine
preparation
weight
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellschaft Farbe Bayer
Original Assignee
Bayer 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 Bayer Ag filed Critical Bayer Ag
Publication of CH302907A publication Critical patent/CH302907A/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
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles

Landscapes

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

Description

  

  Verfahren     zur    Herstellung von     1=Amino-3-imino-methylisoindolenin.       Es wurde     gefunden,    dass man ein     1-AmÜ'ö-          3    -     imino    -     methylisoindoleriin        erhalten    kann,  wenn man auf     4=Methylphthalodinitril    Ammo  niak einwirken lässt. Das     1-Amino-3-imino-          methylisoindolenin    bildet lange farblose Pris  men, die sich bei 189 bis 190  C unter Blau  färbung zersetzen.

   Die     !Stellung    der     Methyl          gruppe        ist    nicht sicher bekannt; in Frage       kommt        Stellung    5 oder 6. Es     soll        als        Farb-          stoffzwischenprodukt    u. a. zur Erzeugung  eines     Phthalocyaninfarbstoffes    auf der Faser       Verwendung    finden.

      <I>Beispiel:</I>  In eine mit 28,1 Gewichtsteilen Benzol ver  dünnte Lösung von 0,29     Gewichtsteilen    Na  trium in 5,05 Gewichtsteilen Methanol trägt  man unter Rühren bei 20  C 7,1     Gewichtsteile     4 -     Methylphthalodinitril    ein und rührt bei  20  C so     lange,    bis sich die Lösung nicht mehr  tiefer gelb färbt.

   Hierauf fügt man 1,28 Ge  wichtsteile     Ammoniak    100prozentig, gelöst in  Methanol, hinzu und rührt weiter, bis eine    Probe     mit        verd%NI.üu        Natronkxugd        Na-          triumhydrosulfit    keine blaue     Leukoverbindung     mehr gibt. Das     auskristallisierte        Methyll-          amino-3-iminoisoindolenin    wird abgesaugt und  mit Benzol und     Ligroin    gewaschen.

   Es bildet  farblose, kräftige, lange Prismen, welche sich  bei 170  C grünblau färben, bei 181 bis     182     C  sintern und sich bei 189     bis        194     C unter  Blaufärbung zersetzen.  



  Die in der ursprünglichen     Reaktionsflüs-          sigkeit    noch gelösten Anteile der Base lassen  sich mit     Ameisensäure        als        Formiat    ausfällen,  welches durch Auflösen in     Wasser        und    Fällen  mit Aceton gereinigt     werden    kann.



  Process for the preparation of 1 = amino-3-imino-methylisoindolenine. It has been found that a 1-AmÜ'ö- 3 - imino - methylisoindoleriin can be obtained if ammonia is allowed to act on 4 = methylphthalodinitrile. The 1-amino-3-iminomethylisoindolenine forms colorless prisms for a long time, which decompose at 189 to 190 C with a blue color.

   The position of the methyl group is not known for certain; Position 5 or 6 is possible. It should be used as an intermediate dye product and a. to produce a phthalocyanine dye on the fiber use.

      <I> Example: </I> 7.1 parts by weight of 4-methylphthalodinitrile are introduced into a diluted solution of 0.29 parts by weight of sodium in 5.05 parts by weight of methanol with 28.1 parts by weight of benzene, while stirring at 20 ° C. at 20 C until the solution no longer turns yellow.

   Then add 1.28 parts by weight of 100% ammonia, dissolved in methanol, and stir until a sample with dilute sodium hydroxide solution no longer gives any blue leuco compound. The crystallized methyll-amino-3-iminoisoindolenine is filtered off with suction and washed with benzene and ligroin.

   It forms colorless, strong, long prisms that turn green-blue at 170 C, sinter at 181 to 182 C and decompose at 189 to 194 C to turn blue.



  The proportions of the base still dissolved in the original reaction liquid can be precipitated with formic acid as formate, which can be purified by dissolving in water and precipitating with acetone.

Claims (1)

PATENTAITSPRUCH Verfahren zur Herstellung von 1-Amino- 3-imino-methylisoindolenin, dadurch :gekenn zeichnet, dass man auf 4-12ethylphthalodini- tril Ammoniak einwirken lässt. Die neue Ver bindung bildet lange farblose Prismen, die sich bei 189 bis 190 C unter Blaufärbung zersetzen. PATENT Claim Process for the production of 1-amino-3-imino-methylisoindolenine, characterized in that it is characterized in that ammonia is allowed to act on 4-12-ethylphthalodinitrile. The new connection forms long, colorless prisms which decompose at 189 to 190 C to turn blue.
CH302907D 1949-08-25 1950-08-21 Process for the preparation of 1-amino-3-imino-methylisoindolenine. CH302907A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB302907X 1949-08-25

Publications (1)

Publication Number Publication Date
CH302907A true CH302907A (en) 1954-11-15

Family

ID=10305295

Family Applications (1)

Application Number Title Priority Date Filing Date
CH302907D CH302907A (en) 1949-08-25 1950-08-21 Process for the preparation of 1-amino-3-imino-methylisoindolenine.

Country Status (1)

Country Link
CH (1) CH302907A (en)

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