CH281440A - Process for the production of a quinazoline derivative. - Google Patents

Description

  

  <B> Process for the production of </B> a quinazoline derivative. It has been found that a valuable quinazoline derivative is obtained if 3-cyano-2-cinnamoylamino-anthraquinone is converted into the corresponding quinazoline derivative with phosphorus pentaehloride and this is converted with 4-aminoanthraehinone-2,1- (N) -benzene aeridone implements.



  The new quinazoline derivative dissolves in concentrated sulfuric acid with a brown color and dyes cotton from a purple-brown vat in real bottle-green tones.



  The 3-cyano-2-cinnamoylamino-anthraquinone serving as the starting material in the present process can be obtained in a simple manner by aylating 3-cyano-2-aminoanthraquinone using cinnamic acid chloride. The ring closure to the corresponding quinazoline derivative takes place with the aid of phosphorus penta chloride and can expediently be carried out in an inert medium such as nitrobenzene at an elevated temperature, e.g.

   B. between 150 and the boiling point of nitrobenzene, are performed by. This is how you get the quinazoline derivative of the formula
EMI0001.0026
         1) he implementation of this compound with the 4-aminoanthraehinone-2,1- (N) -benzolacridone can be used with advantage in high-boiling solvents such as nitrobenzene, dichlorobenzene or phenol, at elevated temperature, for. B. means carried out at the boiling point of the solution in question. will.



  <I> Example: </I> 3.8 parts of 2-cinnamoylamino-3-eyananthraquinone of the formula
EMI0001.0033
    (obtainable by heating for one hour 21.5 parts of 2-cinnamoylamino-3-bromoanthraquinone with 5 parts of cuprocyanide and 45 parts of pyridine in 420 parts of nitrobenzene to 185) with 2.5 parts of phosphorus pentahloride in 72 parts of nitrobenzene half a Heated to 180 to 185 hours. After cooling, it is filtered, washed with benzene and dried. A brownish crystal powder is obtained which dissolves in concentrated sulfuric acid with a brown color.



  4.2 parts of the product thus obtained are heated to boiling for a quarter of an hour together with 3.2 parts of 4-aminoanthraquinone-2,1- (N) -benzolacridone in 105 parts of phenol. After adding 105 parts of pyridine, the mixture is allowed to cool to about 60 °, filtered, washed with benzene and dried. The condensation product can be purified by fractional crystallization from sulfuric acid.

 

Claims (1)

PATENT CLAIM: Process for the production of a quinazoline derivative, characterized in that 3-cyano-2-monoylamino-anthraquinone is converted into the corresponding quinazoline derivative with phosphorus pentachloride and this is converted with 4-aminoanthraquinone-2,1- (N) - converts benzene aeridon. The new quinazoline derivative solves. in concentrated sulfuric acid with a brown color and dyes cotton from a violet-brown vat in real bottle green tones. SUBClaims 1. The method according to claim, characterized in that the implementation of 3-cyano-2-cinnamoylamino-anthraquinone is carried out with the phosphorus pentahelron in an inert medium at elevated temperature. 2. The method according to claim, characterized in that the implementation of 3-cyano-2-cinnamoylamino-anthraquinone is carried out with. the phosphorus pentachloride in nitrobenzene between 150 and the boiling point of nitrobenzene. 3. Process according to patent claim, characterized in that the reaction with the .l-aminoanthraehinone \ ?, 1- (N) - benzolacridone is carried out in a high-boiling solvent at an elevated temperature. Process according to patent claim, characterized in that the reaction with the -1-aminoanthraehinone-2,1- (N) - benzolacridone in phenol is carried out at its boiling point.