4-Aminophenol → 4-({2-[2-(5-Nitrofuran-2-yl)ethenyl]quinazolin-4-yl}amino)phenol

Participants

Reaction Steps

A 250 ml Erlenmeyer flask equipped with a magnetic stirrer and oil bath for heating was charged with 8.0 g (0.07 mole) of p-animophenol and 25 ml of dimethylformamide. After the p-aminophenol was dissolved by stirring, 9.05 g (0.03 mole) of 2-[2-(5-nitro-2-furyl)vinyl]-4-chloroquinazoline (IV) was added. The reaction mixture was then heated at 70° C-90°C for 2 hours after which 60 ml of water was added and the solution after cooling was placed in a refrigerator for crystallization. After three days, the brown yellow solid was collected, washed first with water, then methanol and then dried to obtain 7.20 g of product melting at 250°-60°C with decomposition. Recrystallization from a 1:1 dimethylformamide-methanol mixture gave 6.5 g of orange crystals of the purified product which melted at 270°-2°C with decomposition.

Provenance & Evidence