O-Phenylenediamine → Coumarin 7

Participants

Reaction Steps

The diphenyl analog of coumarin 7 was prepared by the dehydration/condensation (J. B. Hendrickson, M. S. Hussoin, J. Org. Chem. 1987, 52, 4139-4140) of o-phenylenediamine with the diphenyl analog of coumarin 343. A solution of 7.9 ml of triflic anhydride in 150 ml methylene chloride was added to a solution of 26.16 g triphenylphosphine oxide in 150 ml methylene chloride at 0° C. under nitrogen atmosphere. The resulting mixture was allowed to come to room temperature and a solution of 2.54 g o-phenylenediamine and 7 g diphenyl analog of coumarin 343 prepared according to the method of Example 2 in 80 ml methylene chloride was added dropwise. The slurry was stirred overnight. The reaction mixture was washed with 5% sodium bicarbonate, water and brine, dried of magnesium sulfate, filtered, and rotary evaporated to remove the solvent. The product was isolated by flash column chromatography in methylene chloride.

Provenance & Evidence