Sodium Hydroxide → 4-(2-Fluoro-4-iodoanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylic acid

Participants

Reaction Conditions

Reaction Steps

4-(2-Fluoro-4-iodo-phenylamino)-1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid ethyl ester was dissolved in EtOH (100 mL) and treated with NaOH (2.60 g, 72.0 mmol). This mixture was stirred at 70° C. for 20 hours. The mixture was cooled to room temperature and solvent was removed under reduced pressure. The residue was acidified with 1N HCl then the resulting precipitate was filtered and washed with water. The solid was dried under high vacuum pump to afford 4-(2-Fluoro-4-iodo-phenylamino)-1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid as a white solid (9.0 g, 96%). 1H NMR [(CD3)2SO, 400 MHz] δ 13.27(v br s, 1H), 9.60 (s, 1H), 8.49 (s, 1H), 7.74 (dd, J=10.1, 1.9 Hz, 1H), 7.59 (dd, J=8.4, 1.7, 0.8 Hz, 1H), 7.29 (dd, J=8.5 Hz, 1H), 5.48 (dd, J=0.7 Hz, 1H), 3.38 (s, 3H). (APCI+) calcd for C13H10FIN2O3 388.13 (M−1), found 386.9.

Provenance & Evidence