Acetic Acid → HCID 58962857, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl 6-chloro-4-(2,4-difluoroanilino)nicotinate (1.00 g, 3.2 mmol) was dissolved in CHCl3 (35 ml) and cooled to 0° C. Me2SO4 (2.45 g, 19.5 mmol) was added dropwise over 5 min. The solution was allowed to warm to room temperature and then refluxed for 18 h. After cooling to room temperature, a mixture of triethylamine (9.9 ml), AcOH (6.6 ml) and EtOH (6.6 ml) was added. The reaction mixture was heated to reflux for a further 2 h then cooled and H2O (50 ml) was added. After partitioning between water and EtOAc, the organic layer was further washed with water, brine, dried (Na2SO4) and concentrated under reduced pressure to give crude ethyl 4-(2,4-difluoroanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylate. Further purification by recrystallisation (EtOAc/Hexane) gave the desired product as a cream solid (0.55 g, 56%); m.p. (EtOAc/Hexane) 128-132° C. 1H NMR [400 MHz, CDCl3] δ 9.15 (br s, 1H), 8.21 (s, 1H), 7.36-7.30 (m, 1H), 6.95-6.87 (m, 2H), 5.66 (s, 1H), 4.35 (q, J=7.1 Hz, 2H), 3.54 (s, 3H), 1.40 (t, J=7.1 Hz, 3H).

Provenance & Evidence