Sodium Nitrate → HCID 12012757, compound

Participants

Reaction Steps

Compound 2 (467 mg, 2 mmol) was added to a stirred solution of sodium nitrate (170 mg, 2 mmol) in trifluoroacetic acid (5 mL) and the mixture was stirred at rt for 4 h. The solution was poured into ice-cold water (100 mL) and extracted with EtOAc. The combined organic phases were washed with saturated aq. NaHCO3 and brine, dried and evaporated. Recrystallization (EtOAc-hexanes) afforded 16 as orange needles (395 mg, 71%), mp 136-137° C.; IR: νmax/cm−1 1740, 1670, 1530; 1H NMR: δH (90 MHz) 7.52 (br s, 1H), 7.36 (br s, 1H), 4.23 (t, J=8.3 Hz, 2H), 3.70 (s, 3H), 3.62 (s, 2H), 3.20 (t, J=8.3 Hz, 2H) and 2.24 (s, 3H). Anal. Calcd for C13H14N2O5: C, 62.94; H, 6.27; N, 4.59. Found: C, 63.00; H, 6.16; N, 4.59.

Provenance & Evidence