HCID 19899911, compound → 4-Fluoro-1,3-dihydro-2H-indol-2-one

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Reaction Steps

(2-fluoro-6-nitrophenyl)acetic acid (3.3 g, 16.6 mmol) was dissolved in acetic acid (20 mL) and hydrogenated over palladium on carbon (10%, 0.5 g) at 50 psi for 24 hours. The catalyst was removed by filtration through the Celite® reagent, which was washed with methanol, and the combined organics were then evaporated. The reaction mixture was then dissolved in ethanol (100 mL), 50 mg of para-toluenesulfonic acid was added, and the mixture heated under reflux for 1 hour. The mixture was poured into water, extracted with ethyl acetate, dried over magnesium sulfate, and evaporated. The solid was triturated with hexane/ethyl acetate (95/5) to give 1.7 g, 67% of 4-fluoro-1,3-dihydro-2H-indol-2-one: HRMS [M+H]+=152.0515

Provenance & Evidence