Sodium Nitrite → HCID 59441694, compound

Participants

Reaction Steps

To the solution of 6-ethoxy-3,4-dihydroquinolin-2(1H)-one (72.3 g, 0.38 mol, 1 equiv) in TFA (800 mL) was added NaNO2 (33.7 g, 0.496 mol, 1.3 equiv) at 0° C. The solution was allowed to warm to room temperature and stirring was continued for 4 hours. The mixture was poured into ice and the yellow precipitate was isolated via filtration and dried under high vacuum at 50° C. The crude product was recrystallized from ethyl acetate to afford 6-(ethyloxy)-7-nitro-3,4-dihydro-2(1H)-quinolinone (69.2 g, 77% yield). 1H NMR (400 MHz, DMSO) δ 1.31 (t, J=6.8 Hz, 3H), 2.45-2.49 (m, 2 H), 2.95 (t, 2 H, J=6.4 Hz), 4.13-4.15 (m, 2 H), 7.25 (s, 1 H), 7.34 (s, 1 H), 10.16 (bs, 1H).

Provenance & Evidence