Water → 1-methyl-6-nitro-3,4-dihydroquinolin-2(1H)-one

Participants

Reaction Steps

To a stirred suspension of 6-nitro-3,4-dihydro-1H-quinolin-2-one (Step 1, 990 mg, 5.15 mmol) in DMF (3.0 mL) is added K2CO3 (855 mg, 1.2 equiv.) followed by Mel (0.64 mL, 2.0 equiv.). The resulting solution is stirred overnight at room temperature. Water (20 mL) is then added and the reaction mixture is extracted with ethyl acetate (20 mL×2) and washed with saline (20 mL). The organic layers are collected and dried over MgSO4. Solvent is removed to yield the title compound as a yellow solid (956 mg, 90%). 1H NMR (300 MHz, DMSO) δ 8.16-7.26 (m, 3H), 3.30 (s, 3H), 3.00 (t, 2H), 2.61 (m, 2H).

Provenance & Evidence