1-Bromo-5-nitronaphthalene → 5-Bromonaphthalen-1-amine

関与物質

反応条件

反応手順

To the solution of 5-nitro-1-bromonaphthalene (A) (2.5 g, 10 mmol) in EtOH/AcOH /Dioxane/H2O (2:2:2:1) (30 mL) was added Fe (5.6 g, 100 mmol) and 2 drops of 2 N HCl. The reaction mixture was stirred at 100° C. for 2 hrs. After evaporation of solvent, the residue was dissolved in 100 mL DCM and washed with 5% NaHCO3 (3×30 mL) and dried over Na2SO4. After evaporation of solvent, the crude mixture was purified on a silica gel column, eluting with DCM/hexanes (1:1), to give compound B as a white powder (3.0 g, 97%). mp 65-66° C.; 1H NMR (400 MHz, CDCl3) δ 7.79 (d, J=8.8 Hz, 1H), 7.76 (d, J=8.0, 1H), 7.71 (d, J=8.4 Hz, 1H), 7.39 (t, J=7.6 Hz, 1H), 7.28 (t, J=7.2 Hz, 1H), 6.83 (d, J=7.2 Hz, 1 H), 4.18 (s, 2H); 13C NMR (100 MHz, CDCl3) δ 142.5, 133.0, 130.4, 128.0, 125.1, 125.0, 123.9, 121.0, 118.4, 110.9; ESI-MS (m/z) calcd. for C10H9BrN222.0 (M+H)+, found 222.1. Anal. Calcd for C10H8BrN: C, 54.08; H, 3.63; N, 6.31. Found: C, 53.81; H, 3.46; N, 6.11.

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