Nitric Acid → HCID 67492909, compound

Participants

Reaction Steps

A solution of 1-(1-methylpiperidin-4-yl)-3,4-dihydroquinolin-2(1H)-one (305 mg, 1.25 mmol) in conc. H2SO4 (4 mL) was treated with fuming HNO3 (53 μL, 1.25 mmol) at −5 to −10° C. (ice/MeOH) and the resulting solution was stirred for 30 min. at the same temperature. The reaction was quenched with the addition of crushed ice, and then basified with 1 N NaOH, and the product was extracted into CH2Cl2 (2×50 mL). The combined CH2Cl2 layer was dried (Na2SO4), filtered, and the solvent was evaporated. The crude was triturated with hexanes to afford the title compound (320 mg, 88.4%) as a solid. 1H-NMR (CDCl3) δ 8.10-8.05 (m, 2H), 7.33 (d, J=8.7 Hz, 1H), 4.50-4.39 (m, 1H), 3.01-2.90 (m, 4H), 2.67-2.54 (m, 4H), 2.33 (s, 3H), 2.15-2.08 (m, 2H), 1.74-1.70 (m, 2H). MS (ESI): 290.2 (M+1, 100%).

Provenance & Evidence