Aniline → 2-Hydroxy-N-phenyl-11H-benzo[A]carbazole-3-carboxamide

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Reaction Conditions

Reaction Steps

The aromatic ester is reacted with an aniline in a solvent and heating to form the anilide product. The reaction temperature can be varied to from about 140° C. to about 280° C. or above. Specifically, phenyl 2-hydroxy-11H-benzo(a)carbazole-3-carboxylate can be reacted with aniline in methyl N-pyrrolidinone at about 250° C. The ratio of the phenyl ester to aniline can vary, for example, from about 1:1 equivalent and up to about 20 equivalents. After the reaction is completed, the product mixture is cooled to room temperature, about 25° C., and discharged into an acidic aqueous solution, such as a 5 percent HCl ice cold solution. The precipitated anilide product, such as 2-hydroxy-11H-benzo(a)carbazole-3-carboxanilide, is isolated by filtration and washed with water and methanol. Purification can be accomplished by first dissolving the crude product in a hot solvent, such as DMF, and then precipitating the product by adding water or methanol, or a mixture of methanol and water. The purified product is then characterized by melting point, IR, mass spectrometry, NMR spectroscopy, especially 13C NMR as well as elemental analysis.

Provenance & Evidence