Cl.[F:2][C:3]1[C:4]([N+:16]([O-])=O)=[C:5]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH:6]=[C:7]([F:9])[CH:8]=1>O1CCCC1.[Zn]>[F:2][C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[C:5]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[C:4]=1[NH2:16]Concentrated hydrochloric acid (6.3 mL) was added slowly to a mixture of zinc dust (4.9 g) and 4-(3,5-difluoro-2-nitro-phenyl)-morpholine (3.69 g) in tetrahydrofuran (40 mL) cooled to 0° C. The reaction mixture was then stirred for 1 hour at 0° C. and 2 hours at 25° C. The reaction mixture was filtered through Celite (10 g), concentrated in vacuo and purified by flash chromatography to furnish 1.76 g (54% yield) of the title compound as an orange solid. GC-MS (m/z) 215 (M+); tR=5.11. 1H NMR (500 MHz, DMSO-d6): 2.81 (t, 4H), 3.76 (t, 4H), 4.52 (s, 2H), 6.66 (dt, 1H), 6.82 (m, 1H).
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