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

Temperature

0 °C

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.

1. stirringThe resulting solution was stirred at room temperature for 15 hours
2. customquenched by the addition of ethanol (200 mL)
3. concentrationThe mixture was concentrated
4. additionwater (400 mL) was added
5. extractionthe product was extracted with methylene chloride (3×200 mL)
6. dry with materialdried (Na2SO4)
7. filtrationfiltered
8. concentrationconcentrated

ORD record

ord-93f448249ea54970bcd5948385ab2c7b

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07696229B2