Hydrochloric Acid → 3-(4-Fluorophenyl)-5-methyl-1-nitrosoindoline

Participants

Reaction Conditions

Reaction Steps

3-(4-Fluorophenyl)-5-methylindoline (0.7 g, 0.00308 mol) was dissolved in ethanol (4.2 mL) and concentrated hydrochloric acid (4.2 mL) was added at 0° C. The reaction mixture was stirred for 5 min. at 0° C. A solution of sodium nitrite (0.425 g, 0.00616 mol) in water (4.2 mL) was added at 0° C., and the reaction mixture was stirred for 2 h at RT. After completion of reaction (monitored by TLC), solvent was removed under reduced pressure, the residue basified with 10% aq. sodium hydroxide solution and the mixture extracted with EtOAc (3×100 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give desired compound as a brown colored oil (0.6 g, 76% yield).

Provenance & Evidence