Hydrochloric Acid → 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-7-(hydroxymethyl)-3,4-dihydroquinazolin-2(1H)-one

Participants

Reaction Steps

To a stirred solution of methyl 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2,3,4-tetrahydroquinazoline-7-carboxylate (INTERMEDIATE 32) (8.23 g) in THF (140 mL) was added lithium aluminum hydride (14 mL of a 1.0M solution in THF) and the mixture was let stir 1.5 h. More lithium aluminum hydride (4.5 mL of a 1.0M solution in THF) was added and the mixture was stirred overnight. Another portion of lithium aluminum hydride (4.5 mL of a 1.0M solution in THF) was added and stirred 4 h. The reaction was carefully poured into a flask containing 1N aqueous HCl (500 mL) and stirred. To the mixture was added ethyl acetate (500 mL) and the layers were mixed, then separated. The organic layer was washed with brine (300 mL), dried over anhydrous MgSO4, filtered and concentrated. The resulting solid was triturated with hexanes, then CH2Cl2 to give the 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-7-(hydroxymethyl)-3,4-dihydroquinazolin-2(1H)-one compound.

Provenance & Evidence