[NH2:1][C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1[C:14](=[O:16])[CH2:13][CH:12]([Si](F)(C)C)[CH2:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2.[F-].[K+].C(=O)(O)[O-:24].[Na+].OO>CO>[NH2:1][C:2]1[C:3]2[C:8]([N:9]=[C:10]3[C:15]=1[C:14](=[O:16])[CH2:13][CH:12]([OH:24])[CH2:11]3)=[CH:7][CH:6]=[CH:5][CH:4]=2A solution 9-amino-3,4-dihydro-3-(fluorodimethylsilyl)acridin-1(2H)-one (3.7 g) 1:1-tetrahydrofuran:methanol (70 ml), potassium fluoride (7.45 g), and sodium bicarbonate (10.7 g) was chilled in an ice/water bath, and 30% aqueous hydrogen peroxide (44 ml) was added slowly. Upon completion of the addition, the bath was removed and stirring was continued for 3 hr. The reaction mixture was poured into water (250 ml) and a little diethyl ether was added. The mixture was filtered and the filter cake was washed with water and diethyl ether to give 2.6 g (89%) of product, mp 205° C. (dec).
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