Aniline → HCID 14843023, compound

Participants

Reaction Steps

To a solution of 3-(3-indolyl)-N-(2-carboxyphenyl)propionamide (6.20 g, 20 mmol) in 50 ml of THF at room temperature was added 1,1-carbonyldiimidazole (3.26 g, 20 mmol). The reaction mixture was stirred under a dry atmosphere for 30 minutes after which aniline (2 ml, 22 mmol) and PPTS (4.03 g, 16 mmol) were added. The resulting reaction mixture was stirred under reflux for two days. The reaction mixture was allowed to cool and evaporated to dryness in vacuo. The product residue was taken up in ethyl acetate and washed (1N HCl, water, saturated NaHCO3, and brine), dried over anhydrous sodium sulfate, and concentrated in vacuo to a brown oil which crystallized from ethyl acetate/hexanes. The product was recrystallized from methanol/ethyl acetate to provide 2.28 g of 2-[2-(3-indolyl)ethyl]-3-phenyl-4-(3H)quinazolinone as white fluffy needles; m.p. 193°-194° C.; FABMS and EIMS 366 (M+); IR (KBr) 1672 CM-1.

Provenance & Evidence