CH204236A - Process for the preparation of a 2,3-oxynaphthoic acid arylide. - Google Patents

Process for the preparation of a 2,3-oxynaphthoic acid arylide.

Info

Publication number
CH204236A
CH204236A CH204236DA CH204236A CH 204236 A CH204236 A CH 204236A CH 204236D A CH204236D A CH 204236DA CH 204236 A CH204236 A CH 204236A
Authority
CH
Switzerland
Prior art keywords
oxynaphthoic acid
preparation
acid arylide
arylide
production
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 CH204236A publication Critical patent/CH204236A/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/12—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by halogen atoms or by nitro or nitroso groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
    • C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
    • C07C2603/48—Chrysenes; Hydrogenated chrysenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
    • C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
    • C07C2603/50—Pyrenes; Hydrogenated pyrenes

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

Description

  

  Verfahren zur Herstellung eines     2,3-oxynaphthoesäurearylids.       Es wurde gefunden,     dass    ein     2,3-Oxynoph-          thoesäurearylid    hergestellt werden kann,  wenn man<B>1</B>     Mol        2,3-Oxynaphthoesäurehalo-          genid    auf<B>1</B>     Mol        3-Aminopyren    einwirken       lässt.     



  Das neue Produkt bildet ein     blassgelbes     Pulver vom F. 2<B>6</B> 2 bis 2<B>6 5</B>     ',    das sich aus       o-Diehlorbenzol        umkristallisieren        lässt.    Es  löst sich in verdünnten     Ätzalkalien;    die wäs  serige Lösung der Salze zeichnet sieh durch  sehr gute Affinität zur pflanzlichen Faser  aus. Das Kondensationsprodukt stellt ein  wertvolles Zwischenprodukt zur Herstellung  von Farbstoffen dar.  



  <I>Beispiel:</I>  <B>82,5</B> Teile     2,3-Oxynaphthoesäurechlorid     werden unter Rühren in 480 Teilen     Pyridin     bei<B>10'</B>     einaetragen    und 1/2 Stunde bei die  ser Temperatur weitergerührt. Hierauf wer  den<B>88</B> Teile     3-Aminopyren    zugefügt, die  Temperatur auf<B>118 '</B> erhöht und zur Be  endigung der Reaktion noch 2 Stunden bei    dieser Temperatur gerührt. Nach dem Er  kalten wird mit Eis versetzt, mit Schwefel  säure angesäuert, filtriert, mit Wasser und  schliesslich mit Alkohol ausgewaschen.

   Zur  Reinigung wird das Umsetzungsprodukt mit  <B>1 %</B>     iger        Natriumacetatlösung    ausgekocht,  hierauf in einer Reibschale mit Alkohol     an-          geteigt,    Natronlauge     (30%ig)    zugefügt, bis  alles in Lösung gegangen ist und mit 4 Li  ter Wasser von<B>50'</B> verdünnt, Tierkohle zu  gesetzt und filtriert. Das Filtrat wird an  gesäuert, der Niederschlag     abfiltriert,    ge  waschen und getrocknet.  



  Zu demselben Produkt gelangt man, wenn  man     2,3-Oxynaphthoesäure    mit     3-Amino-          pyren    in Gegenwart von indifferenten Ver  teilungsmitteln, wie z. B.     Toluol    und in Ge  genwart von     Phosphortrichlorid    kondensiert.



  Process for the preparation of a 2,3-oxynaphthoic acid arylide. It has been found that a 2,3-oxynophthoic acid arylide can be produced if <B> 1 </B> mole of 2,3-oxynaphthoic acid halide is allowed to act on <B> 1 </B> mole of 3-aminopyrene .



  The new product forms a pale yellow powder of F. 2 <B> 6 </B> 2 to 2 <B> 6 5 </B> ', which can be recrystallized from o-diehlobenzene. It dissolves in dilute caustic alkalis; the aqueous solution of the salts is characterized by a very good affinity for vegetable fibers. The condensation product is a valuable intermediate for the production of dyes.



  <I> Example: </I> <B> 82.5 </B> parts of 2,3-oxynaphthoic acid chloride are introduced into 480 parts of pyridine at <B> 10 '</B> with stirring and for 1/2 hour at the further stirred at this temperature. Then 88 parts of 3-aminopyrene are added, the temperature is increased to 118 and the mixture is stirred at this temperature for a further 2 hours to end the reaction. After cooling, ice is added, acidified with sulfuric acid, filtered, washed with water and finally with alcohol.

   For cleaning, the reaction product is boiled with <B> 1% </B> sodium acetate solution, then made into a paste with alcohol in a mortar, sodium hydroxide solution (30%) is added until everything has dissolved and 4 liters of water are removed <B> 50 '</B> diluted, add animal charcoal and filter. The filtrate is acidified, the precipitate is filtered off, washed and dried.



  The same product is obtained if you 2,3-oxynaphthoic acid with 3-amino pyrene in the presence of indifferent Ver distributing agents such. B. toluene and condensed in Ge presence of phosphorus trichloride.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines 2,3- Oxynaphthoesäurea-rylids, dadurch gehenn- zeiengt, dass man<B>1 Mg!</B> 2,3-Oxynaphtlige- säurehalogenid auf<B>1</B> Mol 3-Aminopyren ein- wirk-en lässt. Das neue Produkt bildet ein blassgelbes Pulver vom F.<B>262</B> bis<B>265</B> ', PATENT CLAIM: A process for the production of a 2,3-oxynaphthoic acid arylide, characterized in that <B> 1 Mg! </B> 2,3-oxynaphthoic acid halide to <B> 1 </B> mol 3- Aminopyrene can act. The new product forms a pale yellow powder from F. <B> 262 </B> to <B> 265 </B> ', das sich aus o-Dichlorbenzol umkristallisieren lässt. Es löst sich in verdünnten Ätzalkalien, die wäs serige Lösung der Salze zeichnet sich durch sehr gutü Affinität zur pflanzlichen Faser aus. Das Kondensationsprodukt stellt ein wertvolles Zwischenprodukt zur Herstellung <B><I>kn</I></B> von Farbstoffen dar. which can be recrystallized from o-dichlorobenzene. It dissolves in dilute caustic alkalis, the aqueous solution of the salts is characterized by a very good affinity for vegetable fibers. The condensation product is a valuable intermediate product in the production of dyes.
CH204236D 1937-06-02 1937-06-02 Process for the preparation of a 2,3-oxynaphthoic acid arylide. CH204236A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH204236T 1937-06-02

Publications (1)

Publication Number Publication Date
CH204236A true CH204236A (en) 1939-04-30

Family

ID=4444057

Family Applications (1)

Application Number Title Priority Date Filing Date
CH204236D CH204236A (en) 1937-06-02 1937-06-02 Process for the preparation of a 2,3-oxynaphthoic acid arylide.

Country Status (1)

Country Link
CH (1) CH204236A (en)

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