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CH212340A - Process for the production of a nitrogen-containing naphthalene derivative. - Google Patents

Process for the production of a nitrogen-containing naphthalene derivative.

Info

Publication number
CH212340A
CH212340A CH212340DA CH212340A CH 212340 A CH212340 A CH 212340A CH 212340D A CH212340D A CH 212340DA CH 212340 A CH212340 A CH 212340A
Authority
CH
Switzerland
Prior art keywords
nitrogen
production
naphthalene derivative
containing naphthalene
yellow
Prior art date
Application number
Other languages
German (de)
Inventor
Gesellschaft Fuer Chemis Basel
Original Assignee
Chem Ind Basel
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 Chem Ind Basel filed Critical Chem Ind Basel
Publication of CH212340A publication Critical patent/CH212340A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
    • C09B5/02—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic ring being only condensed in peri position
    • C09B5/16—Benz-diazabenzanthrones, e.g. anthrapyrimidones
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
    • C09B5/24—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings the heterocyclic rings being only condensed with an anthraquinone nucleus in 1-2 or 2-3 position
    • C09B5/34—Anthraquinone acridones or thioxanthrones
    • C09B5/36—Amino acridones

Landscapes

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

Description

  

  Verfahren zur Herstellung eines     stickstoffhaltigen        Naphthalinderivates.       Es wurde gefunden, dass     ein        stickstoff-          haltiges        Naphthalinderivat    hergestellt werden  kann, wenn man 1     Mol        2,6-Dihalogennaph-          thalin    mit 2     Mol        5-Amino-1,9-anthrapyri-          midin    umsetzt.  



  Das neue Produkt ist ein schwarzblaues       kristallines    Pulver, das sich     in    konzentrier  ter Schwefelsäure mit gelbgrüner Farbe löst,  bei 460   noch nicht schmilzt     und    Baumwolle  aus gelbbrauner     Küpe    blau färbt. Es stellt  überdies ein wertvolles Zwischenprodukt für  die Herstellung von     Küpenfarbstoffen    dar.  



  Als     2,6-Dihalogennaphthalin    kann bei  spielsweise     2,6-Dibromnaphthalin    verwendet  werden.  



  Die Umsetzung wird vorteilhaft durch       Erhitzen    der Komponenten     in        Lösungs-    oder  Verdünnungsmitteln, wie z. B.     Amylalkohol,     Nitrobenzol oder Naphthalin, und zweck  mässig in     Anwesenheit    von Katalysatoren,  wie Kupfer oder     Kupferverbindungen,    sowie  von säurebindenden Mitteln, durchgeführt.

           entwässertes        Natriumacetat,    3 Teile wasser  freies     Natriumcarbonat    und 0,26 Teile     Kup-          ferchlorür    werden während 24     Stunden    unter  Rühren in 90 Teilen trockenem     Nitrobenzol     zum Sieden erhitzt. Nun wird heiss     filtriert     und der Rückstand mit     Nitrobenzol,    Benzol  und Alkohol gewaschen, mit     verdünnter     Säure ausgekocht,     filtriert,    gewaschen und  getrocknet.

      <I>Beispiel:</I>  2,86 Teile     2,6-Dibromnaphthalin,    5,43  Teile     5-Amino-1,9-anthrapyrimidin,    3 Teile



  Process for the production of a nitrogen-containing naphthalene derivative. It has been found that a nitrogen-containing naphthalene derivative can be produced if 1 mole of 2,6-dihalo-naphthalene is reacted with 2 moles of 5-amino-1,9-anthrapyrimidine.



  The new product is a black-blue crystalline powder that dissolves in concentrated sulfuric acid with a yellow-green color, does not yet melt at 460 and dyes cotton from a yellow-brown vat blue. It is also a valuable intermediate product for the manufacture of vat dyes.



  2,6-Dibromonaphthalene, for example, can be used as 2,6-dihalonaphthalene.



  The reaction is advantageous by heating the components in solvents or diluents, such as. B. amyl alcohol, nitrobenzene or naphthalene, and conveniently carried out in the presence of catalysts such as copper or copper compounds, and acid-binding agents.

           Dehydrated sodium acetate, 3 parts of anhydrous sodium carbonate and 0.26 part of copper chloride are heated to boiling in 90 parts of dry nitrobenzene for 24 hours while stirring. It is then filtered while hot and the residue is washed with nitrobenzene, benzene and alcohol, boiled with dilute acid, filtered, washed and dried.

      <I> Example: </I> 2.86 parts of 2,6-dibromonaphthalene, 5.43 parts of 5-amino-1,9-anthrapyrimidine, 3 parts

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines stick stoffhaltigen Naphthalinderivates, dadurch gekennzeichnet, dass man 1 Mol 2;6-Di- halogennaphthalin mit 2 Mol 5-Amino-1,9- anthrapyrimidin umsetzt. Das neue Produkt ist ein schwarzblaues kristallines Pulver, das sich in konzentrier ter Schwefelsäure mit gelbgrüner Farbe löst, bei 460 noch nicht schmilzt und Baumwolle aus gelbbrauner Küpe blau färbt. PATENT CLAIM: Process for the production of a nitrogen-containing naphthalene derivative, characterized in that 1 mol of 2; 6-di-halo-naphthalene is reacted with 2 mol of 5-amino-1,9-anthrapyrimidine. The new product is a black-blue crystalline powder that dissolves in concentrated sulfuric acid with a yellow-green color, does not yet melt at 460 and dyes cotton from a yellow-brown vat blue. Es stellt überdies ein wertvolles Zwischenprodukt für die Herstellung von Küpenfarbstoffen dar. It is also a valuable intermediate product for the manufacture of vat dyes.
CH212340D 1937-12-20 1937-12-20 Process for the production of a nitrogen-containing naphthalene derivative. CH212340A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH206427T 1937-12-20
CH212340T 1937-12-20

Publications (1)

Publication Number Publication Date
CH212340A true CH212340A (en) 1940-11-15

Family

ID=25724308

Family Applications (1)

Application Number Title Priority Date Filing Date
CH212340D CH212340A (en) 1937-12-20 1937-12-20 Process for the production of a nitrogen-containing naphthalene derivative.

Country Status (1)

Country Link
CH (1) CH212340A (en)

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