4-Nitro-2H-1,3-benzodioxole → 1,3-Benzodioxol-4-amine

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Reaction Steps

To a solution of 4-nitrobenzo[d][1,3]dioxole (2.0 g, 12 mmol) in ethanol (80 mL) was added Raney Ni (ca. 0.5 g). The mixture was stirred under an atmosphere of hydrogen for 4 hours. The catalyst was removed by filtration and the filtrate was concentrated. The residue was purified by silica gel chromatography (dichloromethane) to afford the product benzo[d][1,3]dioxol-4-amine (1.04 g, yield 63%). 1H NMR (400 MHz, CDCl3) δ ppm 6.64-6.68 (t, 1H, J=8.0 Hz), 6.29-6.35 (dt, 2H, J=0.8 Hz, 6.4 Hz), 5.90 (s, 2H), 3.52 (br, 2H).

Provenance & Evidence