Cl[C:2]1[N:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10](=[O:12])[N:9]([CH3:13])[C:8]1[CH:14]=[C:15]([Cl:18])[CH:16]=[CH:17][C:7]2=1.[CH3:19][O-:20].[Na+]>CO.O>[Cl:18][C:15]1[CH:16]=[CH:17][C:7]2[C:6]3[C:11](=[C:2]([O:20][CH3:19])[N:3]=[CH:4][CH:5]=3)[C:10](=[O:12])[N:9]([CH3:13])[C:8]=2[CH:14]=1To a solution of 4,8-dichloro-6-methylbenzo[c][2,7]naphthyridin-5(6H)-one (1.0 g, 3.58 mmol) in MeOH (1 mL) was added sodium methoxide (0.806 mL, 3.58 mmol). The resultant mixture was heated in a microwave at 80° C. for 25 min. The reaction mixture was then diluted with water (20 mL) and extracted with ethyl acetate (30 mL). The organic layer was separated, dried over sodium sulphate and evaporated to dryness to afford 8-chloro-4-methoxy-6-methylbenzo[c][2,7]naphthyridin-5(6H)-one (0.4 g, 1.391 mmol, 39% crude yield) as a brown solid. The material was carried on without further purification. LC/MS (ESI) m/e 274.8 [(M+H)+, calcd for C14H12ClN2O2, 275.0]; LC/MS retention time (method C): tR=2.06 min.
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