Methyl iodide → 1-Methyl-7-benzoylindoline

Participants

Reaction Conditions

Reaction Steps

To a stirred slurry of 4.8 grams (0.1 mole) of 50% sodium hydride/oil in 100 ml. of dimethylformamide is added dropwise a solution of 22.3 grams (0.1 mole) of 7-benzoylindoline in 50 ml of dimethylformamide. After addition is complete, the mixture is warmed at 50° C. until all solids dissolve. While maintaining the mixture at 50° C., 9.5 grams (0.1 mole) of methyl iodide is added dropwise to the mixture. The mixture is stirred for 4 hours. The mixture is poured into 2 liters of ice water and extracted with 3 portions of 300 ml of benzene. The benzene extracts are combined, washed with water, dried over sodium sulfate and concentrated to give 1-methyl-7-benzoylindoline as a residue.

Provenance & Evidence