Hydrochloric Acid → 2,3-Dihydro-3-(2-methoxyethyl)-1H-indole

Temperature

0 °C

Under a nitrogen atmosphere 12.6 mL (12.6 mmol) of a 1M borane in THF solution was added dropwise to 1.2 g (6.3 mmol) 3-(2-methoxy-ethyl)-1,3-dihydro-indol-2-one in 50 mL THF. The reaction mixture was refluxed for 3 h, cooled to 0° C. and combined with 10 mL methanol and then with 15 mL semi-concentrated hydrochloric acid solution. The reaction mixture was refluxed for 3 h with stirring, cooled and washed twice with ethyl acetate. The aqueous phase was made alkaline with an aqueous 4M sodium hydroxide solution and extracted three times with ethyl acetate. The organic phases were combined, dried on sodium sulphate and evaporated down.

1. temperatureThe reaction mixture was refluxed for 3 h
2. temperatureThe reaction mixture was refluxed for 3 h
3. temperaturecooled
4. washwashed twice with ethyl acetate
5. extractionextracted three times with ethyl acetate
6. customdried on sodium sulphate
7. customevaporated down

ORD record

ord-e203a9c657464679b59233d0e6934e1e

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08829006B2