反应详情

To a suspension of 48.94 g (0.3 tool) of 3-nitro-5-aminobenzonitrile in 500 mL of CH2Cl2 was added 63 mL of Et3N, 3 g DMAP and lastly, dropwise, 45.5 g (0.45 mol) of butyryl chloride. A mild exothermic reaction ensued. The mixture was allowed to stir for 2 days (monitored by TLC with 50% EtOAc/hexanes). The solution was washed with 1N HCl (2×100 mL), water (1×100 mL), saturated NaHCO3 (2×100 mL), brine (1×100 mL) and dried over MgSO4. The suspension was filtered and concentrated in vacuo. The residue was suspended in a mixture of 600 mL of MeOH and 200 mL of water in a three neck round bottom flask. To this was added gradually 140 mL of 5N NaOH (0.7 mol) solution followed by the dropwise addition of 80 mL of 30% H2O2 (0.7 mmol) solution (exothermic). The mixture was refluxed overnight, cooled to room temperature and filtered. The filtrate was acidified with 1N HCl cooled to 5° C. and filtered. The quinazolinone was recrystallized from hot MeOH to give 38 g (54%) of the title compound as pale brown fine crystals.

1. customA mild exothermic reaction
2. washThe solution was washed with 1N HCl (2×100 mL), water (1×100 mL), saturated NaHCO3 (2×100 mL), brine (1×100 mL)
3. dry with materialdried over MgSO4
4. filtrationThe suspension was filtered
5. concentrationconcentrated in vacuo
6. additionThe residue was suspended in a mixture of 600 mL of MeOH and 200 mL of water in a three neck round bottom flask
7. temperatureThe mixture was refluxed overnight
8. filtrationfiltered
9. temperaturecooled to 5° C.
10. filtrationfiltered
11. customThe quinazolinone was recrystallized from hot MeOH