Nitric Acid → 5-Iodo-6-methyl-2-oxo-1-(3-(trifluoromethyl)phenyl)-1,2-dihydropyridine-3-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

To 6-methyl-2-oxo-1-[3-(trifluoromethyl)phenyl]-1,2-dihydropyridine-3-carboxylic acid (28.6 kg, 1 mol eq, limiting reagent) was added sodium iodide (15.1 kg, 1.05 mol eq) and acetic acid (200.2 L, 7 rel vol). 90% Nitric acid (20.1 kg, 3.0 mol eq) was added dropwise. The reaction was heated to 50° C. and stirred until an HPLC assay showed reaction to be complete. The reaction was cooled and stirred. The precipitated product was collected by filtration, washed with water (171.6 L, 6 rel vol) and dried to constant weight to yield the title compound (19.2 kg, 45.4 mol, 68%); 1H NMR (CDCl3): δ 2.36 (s, 3H); 7.42 (d, 1H, J=8.1 Hz); 7.50 (s, 1H); 7.78 (t, 1H, J=7.8 Hz); 7.85 (d, 1H, J=7.9 Hz); 8.86 (s, 1H); 13.44 (s, 1H) ppm; LCMS: m/z 424.0 (MH+).

Provenance & Evidence