Acetone → 4-[(2-Cyanopropan-2-yl)amino]-2-fluoro-N-methylbenzamide

Participants

Reaction Conditions

Reaction Steps

N-methyl-2-fluoro-4-aminobenzamide 4a (1.68 g, 10 mmol) was added a TMS-CN (4.93 g 50 mmol) solution in acetone (30 mL). The reaction mixture was stirred at 80° C. for 12 h, then concentrated in vacuo. The residue was diluted with water (50 mL). The suspension was extracted with ethyl acetate (3×30 mL). Combined organic layers were washed with brine (3×50 mL), dried (MgSO4) and concentrated in vacuo to dryness. The resulting residue was triturated with a mixed solvent of hexanes and ethylether (20 mL-20 mL). The solid was collected by filtration, affording the title compound 6b (1.8 g, 79% yield). MS (ES-API Negative): 234 (M−H)−.

Provenance & Evidence