[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:14]3[C:9](=[CH:10][N:11]=[C:12]([NH:15][C:16](=[O:18])[CH3:17])[CH:13]=3)[CH2:8][N:7]([CH3:19])[C:6]=2[CH:20]=1.[Mn]([O-])([O-])(=O)=[O:22].[Ba+2]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:14]3[C:9](=[CH:10][N:11]=[C:12]([NH:15][C:16](=[O:18])[CH3:17])[CH:13]=3)[C:8](=[O:22])[N:7]([CH3:19])[C:6]=2[CH:20]=1To a stirred solution of N-(8-chloro-6-methyl-5,6-dihydrobenzo[c][2,7]naphthyridin-2-yl)acetamide (0.6 g, 1.199 mmol) in DCM (20 mL) at rt was added barium manganate (1.536 g, 5.99 mmol) in three portions and the reaction was heated at 45° C. for 60 h. After the completion of reaction, the reaction mixture was diluted with DCM (70 mL) and passed through diatomaceous earth (Celite®). The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (DCM/MeOH as an eluant) to yield N-(8-chloro-6-methyl-5-oxo-5,6-dihydrobenzo[c][2,7]naphthyridin-2-yl)acetamide (0.4 g, 1.071 mmol, 89% yield) as an off white solid. LC/MS (ESI) m/e 302.1 [(M+H)+, calcd for C15H13ClN3O2 302.1]; LC/MS retention time (method C): tR=1.88 min; HPLC retention time (method A); tR=8.82 min; HPLC retention time (method B): tR=7.99 min; 1H NMR (400 MHz, DMSO-d6) δ 11.01 (s, 1H), 9.24 (s, 1H), 8.92 (s, 1H), 8.26 (d, J=8.80 Hz, 1H), 7.69 (d, J=2.00 Hz, 1H), 7.48 (dd, J=2.00, 8.80 Hz, 1H), 3.68 (s, 3H), 2.20 (s, 3H).
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