Sodium hydride → (5-Nitro-3,4-dihydro-2H-benzo[1,4]oxazin-3-yl)-methanol

Beteiligte Stoffe

Reaktionsschritte

To a solution of 2-nitro-6-oxiranylmethoxy-phenylamine (14.7 g, 0.070 mol) in DMF (200 mL) was added sodium hydride (3.5 g, 60 wt. %, 0.087 mol). The resulting reaction mixture was stirred at room temperature overnight. The mixture was evaporated in vacuum, the residue diluted with water (200 mL) and extracted with methylene chloride (2×200 mL). The combined organic layers were washed with water (300 mL) and saturated sodium chloride solution (300 mL), dried (Na2SO4) and concentrated to provide the title compound as a dark red crystal (11.0 g). 1H NMR (DMSO-d6): δ 8.30 (d, 1H); 7.60 (dd, 1H); 7.00 (dd, 1H); 6.65 (dd, 1H); 5.15 (t, 1H); 4.10 (m, 2H); 3.70 (m, 1H); 3.50 (m, 2H).

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