Dimethylformamide → Ethyl 1-butyl-6-iodo-4-oxo-1,4-dihydro-3-quinolinecarboxylate

Participants

Reaction Conditions

Reaction Steps

A suspension of (Z)-ethyl 3-(dimethylamino)-2-(2-fluoro-5-iodobenzoyl)acrylate (WO2006/010733, 415 mg, 1.06 mmol) in ethanol (6 mL) at room temperature was treated with N-butylamine (0.115 mL, 1.17 mmol). The reaction mixture was stirred until a yellow solution resulted, then concentrated under reduced pressure after 1 h. Potassium carbonate (220 mg, 1.59 mmol) and DMF (4 mL) were added to the concentrate, and the reaction mixture was heated to 70° C. for 3 h, cooled to room temperature, and allowed to stand overnight. The next day the reaction mixture was poured into water, and the solid that formed was collected by filtration, washed with water, dissolved in methylene chloride and concentrated under reduced pressure to give title compound which was placed on high vac to remove residual solvent. MS (ESP): 400 (M+H+) for C16H18INO3; NMR: 0.90 (t, J=7 Hz, 3H), 1.28 (t, J=6 Hz, 3H), 1.33 (m, 2H), 1.71 (m, 2H), 4.22 (q, J=7 Hz, 2H), 4.35 (m, 2H), 7.64 (m, 1H), 8.05 (m, 1H), 8.50 (m, 1H), 8.70 (s, 1H).

Provenance & Evidence