[F:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:14]=1[N:13]([CH3:15])[C:12]1[CH2:11][CH2:10][CH2:9][C:8](=[N:16]O)[C:7]2=1.[OH2:18]>O1CCOCC1.CO>[F:1][C:2]1[C:14]2[N:13]([CH3:15])[C:12]3[CH2:11][CH2:10][CH2:9][NH:16][C:8](=[O:18])[C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1A mixture of 8-fluoro-1,2,3,9-tetrahydro-9-methyl-4H-carbazol-4-one oxime (1.8 g) and polyphosphoric acid (ca. 20 ml) in dioxan (30 ml) was stirred under nitrogen at 100°-110° for 1 h. After cooling, the reaction mixture was poured into iced water (1 l) and the resulting suspension was extracted with dichloromethane. The organic extract was concentrated in vacuo to give a solid which was taken up in methanol and adsorbed onto silica. Purification by FCC eluting with System A (200:8:1) gave the title compound (850 mg), m.p. 233°-235°.
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