[F:1][C:2]1[CH:10]=[C:9]2[C:5](/[C:6](=[CH:12]/[C:13]3[N:17]([CH3:18])[N:16]=[CH:15][N:14]=3)/[O:7][C:8]2=O)=[C:4]([N+:19]([O-])=O)[CH:3]=1.O.[NH2:23][NH2:24].C(O)(=O)C>C1COCC1.O>[NH2:19][C:4]1[CH:3]=[C:2]([F:1])[CH:10]=[C:9]2[C:5]=1[C:6]([CH2:12][C:13]1[N:17]([CH3:18])[N:16]=[CH:15][N:14]=1)=[N:23][NH:24][C:8]2=[O:7]
To a solution of 6-fluoro-3-((1-methyl-1H-1,2,4-triazol-3-yl)methylene)-4-nitroiso-benzofuran-1(3H)-one (3) (4.0 g, 135 mmol) in THF (100 mL) was added hydrazine monohydrate (85%) (6 mL) at room temperature under nitrogen atmosphere. The mixture was stirred for 2 hours, then acetic acid (6 mL) was added and the mixture was heated to and kept at 60° C. for 18 hours. The resulting mixture was diluted with water (100 mL) and extracted with ethyl acetate (100 mL×3). The organic layer was dried over anhydrous Na2SO4 and evaporated to dryness to afford the title compound as a yellow solid (1.6 g, yield 42%). LC-MS (ESI) m/z: 275 (M+1)+.
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