ethyl 3-(2-fluorophenyl)-2-methyl-3-oxopropanoate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Prepared according to procedure R using aniline (0.91 mL, 10 mmol) and ethyl 3-(2-fluorophenyl)-2-methyl-3-oxopropanoate (4 g, 20 mmol) in PPA (4 g, 40 mmol). The resulting precipitate was collected by filtration, washed with water, and dried to give 2-(2-fluorophenyl)-3-methylquinolin-4-ol. Mass Spectrum (ESI) m/e=254 (M+1). Prepared The resulting precipitate was collected by filtration washed with water dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of ethyl 3-(2-fluorophenyl)-3-oxopropanoate (4.2 g, 20 mmol) in DMF (30 mL) at 0° C. was added K2CO3 (3.87 g, 28 mmol) portionwise and the mixture was stirred for 30 minutes. After this time iodomethane (1.49 mL, 24 mmol) was added and the reaction mixture was allowed to warm to rt for 2 h. After this time the reaction was treated with 50 mL AcOH/water (5 mL AcOH/45 mL water). The mixture was extracted with EtOAc and the organic layer was washed with brine, dried over Mg2SO4, filtered and evaporated in vacuo to give ethyl 3-(2-fluorophenyl)-2-methyl-3-oxopropanoate. Observed some dimethyl product. Used as crude for the next step. Mass Spectrum (ESI) m/e=225 (M+1). The mixture was extracted with EtOAc the organic layer was washed with brine dried over Mg2SO4 filtered evaporated in vacuo