P-Anisidine → 3-[(4-methoxyphenyl)amino]-4-phenyl-1H-pyrrole-2,5-dione

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-chloro-4-phenyl-1H-pyrrole-2,5-dione (4.84 mmol, 1.0 g) in dry DMF (5 mL) was added 4-methoxyaniline (4.87 mmol, 600 mg) and the reaction mixture was subjected to microwave heating single node 150° C., 15 min, followed by 150° C., 10 min. The solvent was evaporated, and the crude mixture was partitioned between dichloromethane and water. The organic phase was dried over anhydrous Na2SO4, concentrated and the residue was purified on SiO2 (Heptane:EtOAc, 3:1→2:1) to give 457 mg (32%) of the title compound. 1H NMR (400 MHz, DMSO-d6) δ 10.62 (s, 1H), 9.27 (s, 1H), 7.09-6.99 (m, 3H), 6.87-6.83 (m, 2H), 6.65-6.60 (m, 2H), 6.52-6.47 (m, 2H), 3.58 (s, 3H).

Provenance & Evidence