[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][N:12]1[C:17]2[C:18]([N+:22]([O-])=O)=[CH:19][CH:20]=[CH:21][C:16]=2[O:15][CH2:14][C:13]1=[O:25].O1CCOCC1>CO.[Pd]>[NH2:22][C:18]1[C:17]2[N:12]([CH2:11][C:2]3[CH:3]=[CH:4][C:5]4[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=4)[CH:1]=3)[C:13](=[O:25])[CH2:14][O:15][C:16]=2[CH:21]=[CH:20][CH:19]=1A solution of 4-naphthalen-2-ylmethyl-5-nitro-4H-benzo[1,4]oxazin-3-one, I-59 (0.65 g) in methanol (30 mL) and dioxane (7.0 mL) was hydrogenated in presence of 10% Pd—C at 45 psi for 22 h. Reaction mixture was filtered and the filtrate was concentrated to give 5-Amino-4-naphthalen-2-ylmethyl-4H-benzo[1,4]oxazin-3-one, I-60 (620 mg).
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