5-Nitro-2,3-dihydro-1,4-benzodioxine → 2,3-Dihydro-1,4-benzodioxin-5-amine

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A suspension of 5-nitro-2,3-dihydrobenzo[b][1,4]dioxine (8 g, 0.044 mol) and palladium on carbon (10%, 2 g) in methanol (250 mL) was stirred vigorously under an atmosphere of hydrogen overnight at room temperature. The mixture was filtered through a pad of Celite and then concentrated to give the crude product, which was purified by silica gel column chromatography (petroleum ether/ethyl acetate 9/1) to afford the product 2,3-dihydrobenzo[b][1,4]dioxin-5-amine (6.5 g, yield 97%). 1H NMR (400 MHz, CDCl3) δ ppm 6.61-6.65 (t, 1H, J=8.0 Hz), 6.30-6.33 (dt, 2H, J=1.2 Hz, 2.4 Hz), 4.22-4.27 (m, 4H), 3.75 (s, 2H).

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