Formaldehyde → HCID 19815159, compound

Participants

Reaction Steps

A mixture of N-hydroxy-2-(phenylamino)benzamide (1.4 g, 6.15 mmol), p-toluene sulfonic acid (400 ml), and paraformaldehyde (200 mg, 6.75 mmol) in toluene (50 ml) is stirred at room temperature for 30 minutes. The reaction mixture is heated for 10 minutes (in an oil bath preheated to 120°-130° C.) using a Dean-Stark trap to collect water. The reaction mixture is cooled and diluted with ethyl acetate (50 ml) and is extracted with saturated aqueous NaHCO3 (4×50 ml) and water (50 ml). The organic layer is dried (MgSO4) and evaporated. Recrystallization from EtOAc/hexane gives 0.6 g (40%) of 2,3-dihydro-3-hydroxy-1-phenyl-4(1H)-quinazolinone, mp 156°-160° C.

Provenance & Evidence