METHOD OF PRODUCING 1-HYDROXY-3-R-INDOLE-5,6-DICARBONITRILES Russian patent published in 2014 - IPC C07D209/14 

FIELD: chemistry.

SUBSTANCE: invention relates to a method of producing 1-hydroxy-3-R-indole-5,6-dicarbonitriles of structural formula: where R=C₆H₅ or 4-CH₃C₆H₄, or 4-OCH₃C₆H₄, or 2-thienyl, which includes two steps, wherein at the first step, substituted 4-nitro-5-(2-oxoethyl)phthalonitriles react with phosphorus oxychloride POCl₃, reaction of said reactants takes place at 90…110°C and molar ratio of 1:2-3, respectively, for 2.5-5 hours in a dimethylformamide solution, the reaction mass is then cooled, poured into a cold 5…40% sodium bicarbonate solution, further the crystalline precipitate is filtered and recrystallised from an alcohol, dried on air, and at the second step, tin dichloride solution in concentrated hydrochloric acid at 30…50°C is mixed with intense agitation with the a solution of the obtained 4-substituted 5-nitrophthalonitrile in ethyl alcohol in molar ratio of 2.8-4.5:1, respectively, and reaction time of 1-2 hours, the obtained reaction mass is cooled, the formed precipitate of 1-hydroxy-3-R-indole-5,6-dicarbonitriles is filtered and recrystallised from an alcohol and dried on air.

EFFECT: method of producing indole-dicarbonitriles, which can be used as precursors for synthesis of biologically active substances, for synthesis of phthalocyanines and hexazocyclanes.

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