[Br:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:22]3[C:21](=O)[CH2:20][CH2:19][CH2:18][C:17]=3[NH:16][C:15]3[CH2:14][CH2:13][CH2:12][C:11](=[O:24])[C:10]2=3)[CH:5]=[CH:6][C:7]=1[F:8].[BH4-].[Na+].C(O)C>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:10]3[C:11](=[O:24])[CH2:12][CH2:13][CH2:14][C:15]=3[NH:16][C:17]3[CH2:18][CH2:19][CH2:20][CH2:21][C:22]2=3)[CH:5]=[CH:6][C:7]=1[F:8]A mixture of 9-(3-bromo-4-fluorophenyl)-3,4,6,7,9,10-hexahydro-1,8(2H,5H)-acridinedione (1.8 g), sodium borohydride (1.74 g), ethanol (40 mL) and pyridine (14 mL) was heated at 70° C. for three and one half hours. The solvent was removed, the residue partitioned between water and ethyl acetate, the organic layer dried and the solvent removed. Chromatography (methylene chloride/ethyl acetate; 7/3) gave the title compound (1.1 g), as a yellow solid, mp 254°-257° C.; NMR: 1.41-1.51 (m,3, CH2), 1.60-1.88 (m,5, CH2), 2.03-2.13 (m,4, CH2), 2.38-2.44 (m,2, CH2), 4.18 (s,1, CH), 7.13-7.24 (m,2, Ar), 7.38 (dd,1, J=6.9, 2.0, Ar), 8.45 (s,1, NH); (CI, CH4) MS: m/z=378(M+1). Analysis for C19H19FBr: Calculated C, 60.65; H, 5.09; N, 3.72; Found: C, 60.68; H, 5.09; N, 3.65.
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