Ammonia → 8-isopropyl-7-methoxyquinazolin-2(1H)-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-amino-7-methoxy-8-(2-propyl)quinazoline (1.3 g) in tetrafluoroboric acid (50 mL), sodium nitrite solution (2.6 g in 10 mL of water) was added dropwise at 0° C. The reaction mixture was stirred at 0° C. for 1 hour and at room temperature for 18 hours. The reaction mixture was cooled in an ice bath and neutralized with 30% ammonia solution. The product was extracted with ethyl acetate (3×50 mL), combined organic extract was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give the title compound as an off-white solid (1.2 g, 92.3%). mp 188–190° C. (decom); 1H NMR (CDCl3): δ 1.32 (d, 6H, 2×CH3), 3.44 (m, 1H, CH), 3.97 (s, 3H, OCH3), 6.88 (d, 1H, Ar-H, J=8.8 Hz), 7.59 (d, 1H, Ar-H, 8.8 Hz), 9.0 (s, 1H, Ar-H), 9.1 (brs, 1H, NH).

Provenance & Evidence