Hydrazine hydrate (1:1) → HCID 66788042, compound

Participants

Reaction Conditions

Reaction Steps

4-Cyclopropyl-1-methyl-1H-indole-2,3-dione (1.0 g, 4.2 mmol) was treated with hydrazine hydrate (7.0 mL, 225 mmol). The reaction was heated to 130° C. and stirred for 4 hours, at which time the reaction temperature was elevated to 150° C. for another 1.5 hours. The reaction was then placed at room temperature and cooled by the addition of ice. Once the reaction was cooled to room temperature it was diluted with dichloromethane and water and the layers were separated. The aqueous layer was extracted an additional two times with dichloromethane, and the organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated. The resulting residue was purified by silica gel flash chromatography (ethyl acetate-heptane, 0 to 60%) to afford 4-cyclopropyl-1-methyl-1,3-dihydro-indol-2-one; MS: (ES+) ink 188.4 (M+H)+.

Provenance & Evidence