1-(4-Fluoro-5-nitroindolin-1-yl)ethan-1-one → 4-fluoro-5-nitro-2,3-dihydro-1H-indole

A mixture of 1-(4-fluoro-5-nitro-indolin-1-yl)ethanone (0.56 g, 2.51 mmol) and concentrated hydrochloric acid (10 mL) was refluxed for 16 h. The reaction mixture was cooled to ambient temperature and partitioned between chlorofolin (100 mL) and water (100 mL). The organic layer was separated and the aqueous layer extracted with chloroform (5×30 mL). The combined organic layers were washed with water (3×20 mL), brine (3×20 mL) and dried over anhydrous sodium sulphate. Concentration in vacuo afforded 4-fluoro-5-nitro-indoline (0.35 g, 76%) as a yellow solid.

1. temperaturewas refluxed for 16 h
2. custompartitioned between chlorofolin (100 mL) and water (100 mL)
3. customThe organic layer was separated
4. extractionthe aqueous layer extracted with chloroform (5×30 mL)
5. washThe combined organic layers were washed with water (3×20 mL), brine (3×20 mL)
6. dry with materialdried over anhydrous sodium sulphate
7. concentrationConcentration in vacuo

ORD record

ord-d5c18692c104410180fc1db0fbdfbaa3

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08993574B2