Author Topic: salycilic acid to anthranillic acid ?  (Read 3948 times)

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salycilic acid to anthranillic acid ?
« on: April 24, 2004, 09:16:00 AM »
phenol does not react with ammonia to form aniline. resorcinol does react with ammonia at 140C to form meta hydroxy aniline. phlorglucinol reacts with ammonia at room temperature to form 3,5 dihydroxy aniline (maybe a second hydroxyl group could be replaced by heating to 140C).
   this is because the ketonic tautomer becomes more predominant because of conjugation, and it is the ketonic tautomer which reacts with the ammonia.
   in salycilic acid the carbonyl group has a carbon oxygen double bond in position to conjugate with the hydroxyl carbon. could this increase the ketonic tautomer of the hydroxyl group to the point where it could be replaced with an amine group? is there any literature which gives the ratio of keto to enol for the hydroxyl group in salycilic acid, and is it more or less than resorcinol?