Methyl iodide → 1-Methyl-2,3-dihydro-1H-indole

Participants

Reaction Conditions

Reaction Steps

NaH (15 g, 375.00 mmol) was added in several batches to a chilled (0° C.) solution of indoline (30 g, 252.10 mmol) in tetrahydrofuran (400 mL). Methyl iodide (53 g, 373.24 mmol) was then added dropwise with stirring, while maintaining the temperature of 0° C. The resulting solution was stirred at room temperature for 15 hours, then quenched by the addition of ethanol (200 mL). The mixture was concentrated, water (400 mL) was added, and the product was extracted with methylene chloride (3×200 mL). The organics were combined, dried (Na2SO4), filtered and concentrated to provide 20.4 g (60%) of 1-methylindoline as a brown liquid.

Provenance & Evidence