4-Aminophenol → HCID 136160072, compound

Participants

Reaction Steps

A mixture of 448 mg (2 mmol) of 4-chloro-6,7-dimethoxyquinazoline (7) and 2.5 mmol of 4-hydroxyaniline in 20 ml of alcohol (EtOH or MeOH) was refluxed for 8 hours. After cooling triethylamine was added to basify the solution, and the solvent was concentrated to give material that was recrystallized from DMF to give compound (1); 84.29%; m.p. 245.0-248.0° C.; 1H NMR (DMSO-d6): δ 11.21(s, 1H, —NH), 9.70(s, 1H, —OH), 8.74(s, 1H, 2-H), 8.22(s, 1H, 5-H), 7.40(d, 2H, J=8.9 Hz, 2′,6′-H), 7.29(s, 1H, 8-H), 6.85(d, 2H, J=8.9 Hz, 3′,5′-H), 3.98(s, 3H, —OCH3), 3.97(s, 3H, —OCH3). UV(MeOH) λmax(e): 203.0, 222.0, 251.0, 320.0 nm. IR(KBr)umax: 3428, 2836, 1635, 1516, 1443, 1234 cm−1.GC/MS m/z 298 (M++1, 100.00), 297(M+, 26.56), 296(M+−1, 12.46).

Provenance & Evidence