Nitric Acid → HCID 18983607, compound

Participants

Reaction Conditions

Reaction Steps

N-Isopropyl 4,4,-dimethyl-2-oxo-quinoline (Compound 39, 472 mg, 2.18 mmol) was added dropwise to H2SO4 (con. 0.3 mL) cooled to -5° C. with a salt-ice bath. To this brown oil was added a mixture of HNO3 (0.16 mL) and H2SO4 (0.65 mL) at a rate so slow that the internal temperature did not exceed 0° C. The resulting dark oil was stirred vigorously for 10 minutes, followed by addition of ice-water. The yellow reaction mixture was extracted with ethyl acetate (2×5 mL). The combined organic layers were washed with NaHCO3 (10%), dried over MgSO4 and concentrated to give yellow solids. 1H NMR d 1.34 (s, 6H), 1.53(d, J=6.8 Hz, 6H), 2.48 (s, 2H), 4.70-4.79 (m, 1H), 7.25 (d, J=6.3 Hz, 1H), 8.10-8.15 (m, 2H).

Provenance & Evidence