ChemicalBook CAS DataBase List 4(3H)-Quinazolinone, 2-(3-hydroxyphenyl)-

4(3H)-Quinazolinone, 2-(3-hydroxyphenyl)- synthesis

7synthesis methods

Product Name:4(3H)-Quinazolinone, 2-(3-hydroxyphenyl)-
CAS Number:911417-23-7
Molecular formula:C14H10N2O2
Molecular Weight:238.24

4(3H)-Quinazolinone, 2-(3-Methoxyphenyl)-

56071-04-6
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4(3H)-Quinazolinone, 2-(3-hydroxyphenyl)-

911417-23-7
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Yield:911417-23-7 100%

Reaction Conditions:

Stage #1: 2-(3-methoxyphenyl)quinazolin-4(3H)-onewith boron tribromide in dichloromethane at -78 - 20; for 4 h;
Stage #2: with methanol in dichloromethane at -78 - 20; for 0.5 h;

Steps:

3

To 2-(3-methoxyphenyl)quinazolin-4(3H)-one (11.6 g, 45.98 mmole) was added OfCH₂Cl₂ (120 mL) and the mixture was cooled to -78 ⁰C. Then, a 1 M solution of BBr₃ in CH₂Cl₂ (60 mL, 60.0 mmol) was added drop wise and the reaction was stirred at - 78 ⁰C for 1 h and then ambient temperature for 3 h. The reaction was re-cooled to - 78 ⁰C and cautiously quenched with MeOH (20 mL). The ice bath was removed and the system allowed to stir at ambient temperature for 0.5 h. The pH was adjusted to 7 with 10 % w/w NaHCO₃ solution. The solid was filtered, washed with ether, dried and then azeotroped from toluene (3 X) and dried under high vacuum overnight to give 2-(3- hydroxyphenyl)quinazolin-4(3H)-one. (11. Og, mmol, 100%).

References:

WO2008/54599,2008,A2 Location in patent:Page/Page column 105