Synthesis of 4-anilinoquinazoline

A solution of 4-chloroquinazoline (164.6 mg, 1.0 mmol) and aniline (279.4 mg, 3.0 mmol) in n-butanol (5.0 mL) was heated at reflux for 1.5 h. After the reaction mixture was concentrated under reduced pressure, the residue was purified by chromatography on silica gel using ethyl acetate: chloroform 2:1 to afford 4-anilinoquinazoline (155 mg, 70% yield, mp. 222–223°C (Lit. 222-224 °C) (Shen et al., 2011). ¹H NMR (DMSO-d₆): 9.80 (s, 1H), 8.59 (s, 1H), 8.56 (d, 1H, J = 8.0 Hz), 7.90-7.75 (m, 4H), 7.64 (t, 1H, J = 8.0 Hz), 7.40 (t, 2H, J = 8.2 Hz), 7.15 (t, 1H, J = 7.4 Hz). ¹³C NMR (DMSO-d₆): 158.8, 154.4, 149.5, 139.1, 133.0, 128.4 (2C), 127.7, 126.2, 123.8, 122.9, 122.5 (2C), 115.1.