6-hydroxy-2-(3-nitrophenyl)quinazolin-4(3H)-one synthesis

6synthesis methods

Product Name:6-hydroxy-2-(3-nitrophenyl)quinazolin-4(3H)-one
CAS Number:371946-32-6
Molecular formula:C14H9N3O4
Molecular Weight:283.24

4(3H)-Quinazolinone, 6-methoxy-2-(3-nitrophenyl)-

911418-31-0
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6-hydroxy-2-(3-nitrophenyl)quinazolin-4(3H)-one

371946-32-6
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Yield:371946-32-6 80%

Reaction Conditions:

with boron tribromide in dichloromethane at -78 - 20;

Steps:

131

To a suspension of 6-methoxy-2-(3-nitrophenyl)quinazolin-4(3H)-one (3.9Og, 13.1 mmol), in CH₂Cl₂ (30 mL) cooled to -78 °C under an atmosphere of N₂ was added BBr₃ as a 1.0M solution in CH₂Cl₂ (20 mL, 20.0 mmol). The resulting mixture was stirred at -78 °C for 1 h, then allowed to warm to RT upon which it was stirred for a further 3 h. The mixture was re-cooled to -78 °C and stirred overnight. The reaction was quenched by the addition of EtOH (60 mL) and allowed to warm to RT. Stirring was continued for 1 h at RT, upon which a precipitate formed. Sat. NaHCO₃ solution was added and the yellow solid was collected via filtration and washed with Et₂O and EtOH and dried under vacuum to give 6-hydroxy-2-(3-nitrophenyl)quinazolin-4(3H)-one (2.96g, 10.5 mmol, 80%). HPLC retention time 5.588 min.

References:

WO2008/54599,2008,A2 Location in patent:Page/Page column 174