Acetone → 3-(4-fluorophenyl)-5-methyl-N-(propan-2-ylidene)indolin-1-amine

Participants

Reaction Conditions

Reaction Steps

3-(4-Fluorophenyl)-5-methyl-1-nitrosoindoline (1.2 g, 0.00468 mol) was dissolved in acetone (60 mL). To this was added saturated ammonium chloride solution (6.0 mL) and the reaction mixture was cooled to 0° C. Zinc dust (1.2 g, 0.0187 mol) was added portionwise over 30 min. at 0° C. After the addition, the reaction mixture was stirred for 1 h at RT. After completion of reaction (monitored by TLC), the reaction mixture was filtered through Celite, solvent was removed under reduced pressure and the residue purified by column chromatography (8% EtOAc:hexane in silica 100-200 mesh, diameter of column—5.0 cm, height of silica—approx. 5 inch) to provide the desired compound as a yellow colored oil (0.78 g, 60% yield).

Provenance & Evidence