CH281754A - Process for the preparation of a 2-oxynaphthalene-3-carboxylic acid arylide. - Google Patents

Process for the preparation of a 2-oxynaphthalene-3-carboxylic acid arylide.

Info

Publication number
CH281754A
CH281754A CH281754DA CH281754A CH 281754 A CH281754 A CH 281754A CH 281754D A CH281754D A CH 281754DA CH 281754 A CH281754 A CH 281754A
Authority
CH
Switzerland
Prior art keywords
carboxylic acid
oxynaphthalene
preparation
starting material
arylide
Prior art date
Application number
Other languages
German (de)
Inventor
Aktiengesellschaft Ciba
Original Assignee
Ciba Geigy
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 Ciba Geigy filed Critical Ciba Geigy
Publication of CH281754A publication Critical patent/CH281754A/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

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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-Oxynaphthalin.3-carbonsäurearylids.       Es wurde gefunden, dass man zu einem       neuen,        wertvollen        2-Oxynaplitlialin-3-earbon-          säureary@id    gelangt, wenn man     2-Oxy-naph-          thalin-3-earbonsäure    oder eines ihrer funktio  nellen Derivate mit     2,6-Dimethyl-l-aminoben-          zol        einsetzt.     



  Das neue     Produkt    kristallisiert aus Alko  hol in weissen Kristallen aus, die bei 190 bis       1S)1"    schmelzen. Es stellt ein     -wertvolles,    zur       Herstellung-    von     Azopignienten    brauchbares       Zwischenprodukt    dar.  



       Als    funktionelle Derivate kommen zum  Beispiel die     Säurehalogenide    in Frage. Die       Umsetzung    mit den     2-Oxynaphthalin-3-car-          borisäurehalogeniden    kann nach üblichen, an  sich bekannten Methoden, z. B. in Gegenwart       säurebindender    Mittel, durchgeführt werden.

    Falls man als Ausgangsstoff die     2-Oxynaph-          tlialin-3-earbonsäure    selbst verwendet, so wird  die     Unisetzung    mit dem     2,6-Dimethyl-7-amino-          berizol        vorteilhaft    in einem indifferenten     Lö-          sungsmittel    und mit Hilfe von     Phosphorhalo-          #geniden    vorgenommen.    <I>Beispiel:</I>         9-1    Teile trockene     2-Oxynaphtlia.liri-3-car-          bonsäure    werden in 600 Teilen wasserfreiem  Chlorbenzol. angerührt.

   Dazu giesst man 60,5  Teile     2,6-Dinietliyl-l-aininobenzol    und erwärmt  auf     120 .    Unter Rühren tropft man     ini    Ver  laufe von zwei Stunden bei 120 bis 130  eine       llisehung    von 30 Teilen     Phosphortrichlorid     und 30 Teilen     wasserfreiem    Chlorbenzol zu  und hält. die Temperatur während acht. Stun  den. Hierauf lässt man auf 80  abkühlen, giesst    600 Teile Wasser zu und destilliert das Chlor  benzol     durch    Einleiten von Wasserdampf ab.

    Zur wässerigen Suspension des Kondensations  produktes gibt man nun so viel     Natriumcar-          bonat    zu, dass     Brillantgelbpapier    schwach ge  rötet wird, lässt unter Rühren erkalten, fil  triert und wäscht das     2-Oxynaphthalin-3-car-          bonsäure-2',6'-dimethylanilid    mit heissem Was  ser aus.



  Process for the preparation of a 2-oxynaphthalene.3-carboxylic acid arylide. It has been found that a new, valuable 2-oxynaplitlialin-3-earbon- säureary @ id, if you get 2-oxy-naphthalin-3-carboxylic acid or one of its functional derivatives with 2,6-dimethyl l-aminobenzene is used.



  The new product crystallizes from alcohol in white crystals which melt at 190 to 1S) 1 ". It is a valuable intermediate product that can be used for the production of azo-signs.



       The acid halides, for example, can be used as functional derivatives. The reaction with the 2-oxynaphthalene-3-carboric acid halides can be carried out by conventional methods known per se, eg. B. in the presence of acid-binding agents.

    If the 2-oxynaphthalene-3-carboxylic acid itself is used as the starting material, the reaction with the 2,6-dimethyl-7-aminoberizole is advantageously carried out in an inert solvent and with the aid of phosphorus halides . <I> Example: </I> 9-1 parts of dry 2-Oxynaphtlia.liri-3-carboxylic acid are dissolved in 600 parts of anhydrous chlorobenzene. touched.

   To this, 60.5 parts of 2,6-dinietliyl-1-aininobenzene are poured and heated to 120. A solution of 30 parts of phosphorus trichloride and 30 parts of anhydrous chlorobenzene is added dropwise over a period of two hours at 120 to 130, with stirring. the temperature during eight. Hours. The mixture is then allowed to cool to 80, 600 parts of water are poured in and the chlorobenzene is distilled off by passing in steam.

    Sufficient sodium carbonate is now added to the aqueous suspension of the condensation product so that brilliant yellow paper is slightly reddened, allowed to cool while stirring, filtered and the 2-oxynaphthalene-3-carboxylic acid-2 ', 6'-dimethylanilide is washed with hot water.

Claims (1)

PATENTANSPRUCH: Verfahren zur Herstellung eines 2-Oxy- riaphthalin-3-earbonsäurearylids, dadurch ge kennzeichnet, dass 2-Oxynaphthalin-3-carbon- säure oder eines ihrer funktionellen Derivate mit 2,6-Dimethyl-l-aminobenzol umgesetzt wird. Das neue Produkt kristallisiert aus Alko hol in weissen Kristallen aus, die bei 190 bis 191 schmelzen. Es stellt ein wertvolles, zur Herstellung von Azopigmenten brauchbares Zwischenprodukt dar. <B>UNTERANSPRÜCHE:</B> 1. PATENT CLAIM: A process for the production of a 2-oxynaphthalene-3-carboxylic acid arylide, characterized in that 2-oxynaphthalene-3-carboxylic acid or one of its functional derivatives is reacted with 2,6-dimethyl-1-aminobenzene. The new product crystallizes from alcohol in white crystals that melt at 190 to 191. It is a valuable intermediate product that can be used for the production of azo pigments. <B> SUBClaims: </B> 1. Verfahren gemäss Patentanspruch, da durch gekennzeichnet, dass man als Ausgangs stoff 2 - Oxy naphthalin- 3 - carbonsäure selbst verwendet und die Umsetzung in einem indif ferenten Lösungsmittel und mit Hilfe von Phosphorhalogeniden durchführt. 2. Verfahren gemäss Patentanspruch, da durch gekennzeichnet, dass man als Ausgangs stoff ein 2-Oxynapht.halin-3-carbonsäurehalo- g enid verwendet. Process according to patent claim, characterized in that the starting material used is 2-oxynaphthalene-3-carboxylic acid itself and the reaction is carried out in an inert solvent and with the aid of phosphorus halides. 2. The method according to claim, characterized in that a 2-Oxynapht.halin-3-carboxylic acid halide is used as the starting material.
CH281754D 1950-01-24 1950-01-24 Process for the preparation of a 2-oxynaphthalene-3-carboxylic acid arylide. CH281754A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CH281754T 1950-01-24

Publications (1)

Publication Number Publication Date
CH281754A true CH281754A (en) 1952-03-31

Family

ID=4483324

Family Applications (1)

Application Number Title Priority Date Filing Date
CH281754D CH281754A (en) 1950-01-24 1950-01-24 Process for the preparation of a 2-oxynaphthalene-3-carboxylic acid arylide.

Country Status (1)

Country Link
CH (1) CH281754A (en)

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