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

Participants

Reaction Steps

The phenyl 2-hydroxy-11H-benzo(a)carbazole-3-carboxylate obtained from Example I (5 grams, 14 millimoles), aniline (27.5 grams, 280 millimoles) and 15 milliliters of N-methyl pyrrolidinone were charged in a 100 milliliter 3-neck flask equipped with a magnetic stirrer and a nitrogen inlet. The resulting mixture was stirred and was heated to reflux at an oil bath temperature of ~250° C. under a nitrogen atmosphere. After 3 hours, TLC analysis revealed that all the starting phenyl ester was consumed. The mixture was cooled to room temperature and was poured into a 1 liter beaker containing 400 milliliters of ice cold 5 percent HCl. The yellow precipitate obtained was isolated by filtration. After washing with water (~200 milliliters) and ~20 milliliters of methanol and vacuum drying, 5.0 grams of crude product resulted. This product was then recrystallized from a mixture of DMF/MeOH/H2O (~30 milliliter each) yielding 4.4 grams (88 percent) of 2-hydroxy-11 H-benzo(a)carbazole-3-carboxanilide.

Provenance & Evidence