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
Links
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
Landscapes
- 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)
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) |
-
1950
- 1950-01-24 CH CH281754D patent/CH281754A/en unknown
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