Acetic Acid → HCID 178438082, compound

Participants

Reaction Conditions

Reaction Steps

H2O2 (70%, 1.5 mL, ca. 30.0 mmol) was added dropwise to a stirred solution of 1-oxide 135 (273 mg, 0.76 mmol) and HOAc (6 mL) at 50° C. and the reaction was stirred at 80° C. for 20 h. The mixture was cooled, water (50 mL) was added and the mixture was extracted with DCM (5×50 mL). The combined organic fraction was dried and the solvent evaporated to give a yellow oil which was treated with Et3N (3 mL) in MeOH (20 mL) at 20° C. for 66 h. The solvent was evaporated and the residue was purified by chromatography, eluting with a gradient (0-5%) of MeOH/DCM, to give 1,4-dioxide 136 (35 mg, 18%) as a yellow solid: mp (MeOH/DCM) 157-158° C.; 1H NMR δ 8.31 (s, 1H, H-9), 8.26 (s, 1H, H-5), 3.72 (br d, J=5.8 Hz, 2H, CH2O), 3.25-3.35 (m, 2H, CH2), 3.20 (q, J=7.5 Hz, 2H, CH2), 3.00-3.10 (m, 2H, CH2), 2.81-2.92 (m, 1H, H-7H), 1.43 (t, J=7.5 Hz, 3H, CH3), OH not observed; HRMS calcd for C13H15N3O3 (M+) m/z 261.1113, found 261.1115. Anal. calcd for C13H15N3O3: C, 59.8; H, 5.8; N, 16.1. Found: C, 59.6; H, 5.9; N, 15.9%.

Provenance & Evidence