CH305333A - Process for the preparation of 1-amino-3-imino-acetyl-aminoisoindolenine. - Google Patents

Process for the preparation of 1-amino-3-imino-acetyl-aminoisoindolenine.

Info

Publication number
CH305333A
CH305333A CH305333DA CH305333A CH 305333 A CH305333 A CH 305333A CH 305333D A CH305333D A CH 305333DA CH 305333 A CH305333 A CH 305333A
Authority
CH
Switzerland
Prior art keywords
amino
imino
acetylamino
aminoisoindolenine
acetyl
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 CH305333A publication Critical patent/CH305333A/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)
  • Coloring (AREA)

Description

  

  Verfahren zur Herstellung von     1-Amino-3-imino-acetyl-aminoisoindolenin.       Es wurde     gefunden,    dass man in analoger       -#Nreise    wie im Hauptpatent ein     1-Amino-3-          imino-acet3Tlamino-isoindolenin    erhalten kann,  wenn man statt     Phthalimid        4-Acetylamino-          phthalimid    verwendet. Das letztere kann wäh  rend der     Reaktion    aus     4-Acetylaminophthal-          säureanhydrid    bzw. der freien     Carbonsäure    ge  bildet werden.  



  Das so erhaltene     1-Amino-3-imino-acetyl-          amino-isoindolenin    zersetzt. sich bei 238  unter  Grünfärbung. Die Stellung der     Acetylamino-          gruppe    ist nicht sicher bekannt; in Frage       kommt    Stellung 5 oder 6. Es soll als     Farb-          stoffzwischenprodukt    unter anderem zur Bil  dung eines     Phthalocyaninfarbstoffes    auf der  Faser benutzt werden.  



  <I>Beispiel:</I>  30 Gewichtsteile     4-Acetylaminophthalirriid     (bzw. die äquivalente Menge der     Carbon-          säure),    44 Gewichtsteile Harnstoff, 40 Ge  wichtsteile     Ammoniumnitrat,    0,2 Gewichtsteile       Ammoniumrnolvbdat    und 15 Gewichtsteile     Ni-          trobenzol    (oder     Orthodiochlorbenzol)    werden  allmählich auf 1.65 bis 170  erhitzt. Nach  3 Stunden wird die Schmelze dick, und es  entsteht ein Brei von feinen gelblichen     Nädel-          chen.     



  Die so erhaltene Suspension des Nitrates  wird bei 8 bis 10  mit etwa 30     Volumteilen     45 %     iger    Natronlauge alkalisch gestellt, wobei  das Nitrat in die freie Base übergeht. Diese  wird abgesaugt. Sie schmilzt bei 238  unter       Crrünfärbung    und Zersetzung.



  Process for the preparation of 1-amino-3-imino-acetyl-aminoisoindolenine. It has been found that a 1-amino-3-imino-acet3-tlamino-isoindolenine can be obtained in an analogous manner to that in the main patent if 4-acetylamino-phthalimide is used instead of phthalimide. The latter can be formed during the reaction from 4-acetylaminophthalic anhydride or the free carboxylic acid.



  The 1-amino-3-imino-acetylamino-isoindolenine thus obtained decomposes. turns green at 238. The position of the acetylamino group is not known for certain; Position 5 or 6 is possible. It is to be used as an intermediate dye product, among other things, for the formation of a phthalocyanine dye on the fiber.



  <I> Example: </I> 30 parts by weight of 4-acetylaminophthalirriide (or the equivalent amount of carboxylic acid), 44 parts by weight of urea, 40 parts by weight of ammonium nitrate, 0.2 parts by weight of ammonium molybdate and 15 parts by weight of nitrobenzene (or orthodiochlorobenzene) are gradually heated to 1.65 to 170. After 3 hours the melt becomes thick and a paste of fine yellowish needles is formed.



  The suspension of the nitrate thus obtained is made alkaline at 8 to 10 with about 30 parts by volume of 45% strength sodium hydroxide solution, the nitrate being converted into the free base. This is sucked off. It melts at 238 with a cream color and decomposition.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung von 1-Amino- 3-imino-acetyl-aminoisoindolenin, dadurch ge kennzeichnet, dass man 4-Acetylamino-phthal- imid, Harnstoff und Aiunoniummolybdat in Gegenwart mindestens äquimolekularer Men gen solcher Anionen, die bei den angewandten Reaktionsbedingungen noch beständig sind, auf höchstens 200 erhitzt und durch Zusatz von Alkalien aus den entstandenen Salzen des 1-Amino-3-imino-acet7lamirro-isoindolenins die freie Base isoliert. PATENT CLAIM: A process for the preparation of 1-amino-3-imino-acetyl-aminoisoindolenine, characterized in that 4-acetylamino-phthalimide, urea and aluminum molybdate in the presence of at least equimolecular amounts of such anions that are still present under the reaction conditions used are stable, heated to a maximum of 200 and the free base is isolated from the resulting salts of 1-amino-3-imino-acet7lamirro-isoindolenine by adding alkalis. Das so erhaltene 1-Anino-3-imin.o-acetyl- amino-isoindolenin zersetzt sieh bei 238 unter Grünfärbung. <B>UNTERANSPRÜCHE:</B> 1. Verfahren nach Patentanspruch, da durch gekennzeichnet, dass man als Anionen Nitrationen verwendet. 2. Verfahren nach Patentanspruch und Unteranspruch 1, dadurch gekennzeichnet, dass man in Gegenwart indifferenter Lösungsmit tel arbeitet. 3. The 1-amino-3-imin.o-acetylamino-isoindolenine thus obtained decomposes at 238 with a green color. <B> SUBClaims: </B> 1. Method according to patent claim, characterized in that nitrate ions are used as anions. 2. The method according to claim and dependent claim 1, characterized in that one works in the presence of indifferent solvents tel. 3. Verfahren nach Patentanspruch und den Unteransprüchen 1 und 2, dadurch ge kennzeichnet, dass man ein 4-Acetylamino- phthalimid verwendet, das während der Reak tion gebildet wurde. Process according to patent claim and dependent claims 1 and 2, characterized in that a 4-acetylamino phthalimide is used which was formed during the reaction.
CH305333D 1949-08-25 1950-08-21 Process for the preparation of 1-amino-3-imino-acetyl-aminoisoindolenine. CH305333A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB305333X 1949-08-25
CH293696T 1950-08-21

Publications (1)

Publication Number Publication Date
CH305333A true CH305333A (en) 1955-02-15

Family

ID=25733404

Family Applications (1)

Application Number Title Priority Date Filing Date
CH305333D CH305333A (en) 1949-08-25 1950-08-21 Process for the preparation of 1-amino-3-imino-acetyl-aminoisoindolenine.

Country Status (1)

Country Link
CH (1) CH305333A (en)

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