2-Fluoroaniline → HCID 13922969, compound

Participants

Reaction Steps

To a solution 2-fluoroaniline (P1) (1.00 g, 9.00 mmol) in MeOH (11.1 mL) at 0° C. was added dimethyl acetylenedicarboxylate (P2) (DMAD, 1.34 mL, 10.8 mmol). The reaction was stirred at room temperature for 2 h. The mixture was concentrated and the residue was purified by silica gel flash chromatography (gradient 0-25% EtOAc in Hex) to give dimethyl (2E)-2-[(2-fluorophenyl)amino]but-2-enedioate (P3) (1.9 g, 83%). ES-MS [M+1]+=254.4. The above compound (1.90 g, 7.50 mmol) was dissolved in Eaton's reagent (8.00 mL, 50.4 mmol) and heated at 55° C. for 1 h. The LC-MS showed clean conversion. The reaction mixture was cooled to room temperature and slowly poured into a cold saturated solution of NaHCO3. The light-yellow precipitate formed was collected by filtration, washed with H2O and dried in vacuum to provide methyl 8-fluoro-4-hydroxyquinoline-2-carboxylate (P4) that gave a mass ion of 222.4 for M+H+.

Provenance & Evidence