DDQ CHCl3 → 4(1H)-Quinazolinone
Reaction equation
CO[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][NH:7][C:6]2=[O:13].C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.C(Cl)(Cl)Cl>>[N:9]1[C:10]2[C:5](=[CH:4][CH:3]=[CH:12][CH:11]=2)[C:6](=[O:13])[NH:7][CH:8]=1Participants
3
Procedure
The Dihydro-(2H)-2-[3-(4-methoxyphenoxy)phenyl]-3-)4-trifluoromethyl benzyl)-6-methoxyquinazoline-4-one, above, was treated with 1.0 mL (0.05 mmol) of 0.05 molar DDQ/CHCl3 suspension and the mixture shaken at room temperature for 3.5-4 hr. The oxidation product was then purified by resin capture (with about 80 mg of VHL aminomethyl polystyrene resin) overnight. The reaction flask was covered with Teflon film. The resin solution was filtered through 30-50 mg of silica gel, washed with 0.5 mL of chloroform. The product was further purified by Prep TLC eluted with 30% ethyl acetate-hexane to give 9.5 mg (36.5%) of the subject quinazolin-4-one as a white solid. 1H-NMR (300 MHz, CDCl3) δ3.82 (s, 3 H), 3.96 (s, 3 H), 5.33 (s, 2 H), 6.80-7.73 (m, 15 H). MS m/z 533 (M+H, 100%).