Triethylamine → HCID 178440202, compound

Participants

Reaction Steps

To a suspension of 48.94 g (0.3 mol) 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.

Provenance & Evidence