[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](=O)[C:7]2=1.Cl.[NH2:18][OH:19]>N1C=CC=CC=1>[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:18][OH:19])[C:7]2=1A mixture of 8-fluoro-1,2,3,9-tetrahydro-9-methyl-4H-carbazol-4-one (3.0 g) and hydroxylamine hydrochloride (2.92 g) in pyridine (ca. 35 ml) was heated at 60° for 3 h. The solution was concentrated in vacuo then azeotropically dried with toluene (2×10 ml). The residue was treated with 8% sodium bicarbonate solution (125 ml) and extracted with ethyl acetate (3×100 ml). The combined extracts were filtered and concentrated in vacuo to give the title compound (1.8 g) as a solid, t.l.c. (System A, 100:8:1) Rf 0.66.
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