[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1)[C:5]#[N:6].O.S(=O)(=O)(O)[OH:15].N>C(O)(C(F)(F)F)=O>[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1)[C:5]([NH2:6])=[O:15]To a solution of 3-fluoro-5-nitrobenzonitrile (1.0 g, 6.02 mmoL) in TFA (8 mL) was added water (1 mL) and conc. sulfuric acid (2 mL). The reaction mixture was heated to 70° C. and stirred for 24 h. Then the reaction mixture was cooled to 0° C. and liquid ammonia solution was added. The solidified solid was filtered through Celite® (diatomaceous earth) and washed with water to obtain 3-fluoro-5-nitrobenzamide (0.400 g, 36%) as an off white solid. Observed mass (M−1): 183.02.
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