[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[C:4]([CH2:11][CH:12]=[CH2:13])[CH:3]=1>CO.[OH-].[OH-].[Pd+2]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([CH2:11][CH2:12][CH3:13])[CH:3]=1To 4-fluoro-1-nitro-2-(2-propen-1-yl)benzene (9.0 g, 50 mmol) in MeOH (100 mL) was added palladium hydroxide on carbon (2 g). The reaction mixture was stirred under H2 (50 psi) at rt overnight. The solution was filtered and concentrated to provide the title compound of step C (7.4 g, 48.3 mmol, 97%). 1H NMR (400 MHz, CDCl3) δ ppm 1.10 (t, J=7.5 Hz, 3H), 1.60-1.70 (m, 2H), 2.45 (t, J=7.2 Hz, 2H), 6.55-6.65 (m, 1H), 6.67-6.81 (m, 2H).
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