1,2-Dimethoxyethane → N-(6-nitro-2,3-dihydro-1H-inden-5-yl)acetamide

Participants

Reaction Conditions

Reaction Steps

A solution of chloride 21 (2.0 g, 9.0 mmol), 2-(1,4-oxazepan-4-yl)ethylamine (292) (1.63 g, 11.3 mmol) and Et3N (1.3 mL, 9.9 mmol) in DME (140 mL) was stirred at reflux temperature for 20 h. The solution was cooled to 20° C., the solvent evaporated and the residue purified by column chromatography, eluting with a gradient (2-6%) of MeOH/DCM, to give (i) starting material 21 (0.5 g, 25%) and (ii) 1-oxide 48 (1.24 g, 42%) as a yellow solid: mp 119-120° C.; 1H NMR δ 8.08 (s, 1H, H-9), 7.40 (s, 1H, H-5), 5.82 (br s, 1H, NH), 3.81 (t, J=6.1 Hz, 2H, CH2O), 3.74 (t, J=4.7 Hz, 2H, CH2), 3.51-3.56 (m, 2H, CH2), 2.97-3.04 (m, 4H, H-6, H-8), 2.73-2.80 (m, 6H, 3×CH2), 2.15 (p, J=7.4 Hz, 2H, H-7), 1.88-1.94 (m, 2H, CH2); 13C NMR δ 158.7, 154.6, 148.8, 143.3, 129.8, 120.5, 114.7, 69.3, 68.7, 57.5, 55.8, 53.6, 38.7, 33.1, 32.3, 30.0, 25.7; HRMS (FAB+) calcd for C17H24N5O2 (MH+) m/z 330.1930, found 330.1937.

Provenance & Evidence