[F:1][C:2]1[C:3]([F:26])=[C:4]2[O:9][CH2:8][C:7]3([CH2:13][CH2:12][CH2:11][CH2:10]3)[N:6]3[CH:14]=[C:15]([C:23]([OH:25])=[O:24])[C:16](=[O:22])[C:17]([C:18]=1[N+:19]([O-])=O)=[C:5]23.CN(C=O)C>C(O)C.C(O)(=O)C.[Pd]>[NH2:19][C:18]1[C:17]2[C:16](=[O:22])[C:15]([C:23]([OH:25])=[O:24])=[CH:14][N:6]3[C:7]4([CH2:13][CH2:12][CH2:11][CH2:10]4)[CH2:8][O:9][C:4]([C:5]=23)=[C:3]([F:26])[C:2]=1[F:1]A solution of 9′,10′-difluoro-8′-nitro-7′-oxospiro[cyclopentane-1,3′ (2′H)-[7H]pyrido[1,2,3-de][1,4]benzoxazine]-6′-carboxylic acid (3.9 g, 0.01 mmol) in ethanol/acetic acid (1:1, v/v, 100 mL) was hydrogenated under atmospheric pressure over 10% Pd/C (390 mg) at 80° C. for 18 h. Then 200 mL of DMF were added and the reaction mixture was heated until it became clear. The catalyst was removed by filtration over Celite, which was washed two times with hot DMF and the combined filtrates were concentrated in vacuo to dryness to yield the title compound (2.85 g, 73%) which was used crude in the next step.
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