Hydrochloric Acid → 2-(5-Methoxy-2-nitrophenyl)ethan-1-amine

Under a nitrogen atmosphere 200 mL (200 mmol) of a 1M borane in THF solution were slowly added dropwise at RT to 12.6 g (65.7 mmol) (5-methoxy-2-nitrophenyl)-acetonitrile in 380 mL THF. The reaction mixture was refluxed for 2 h. After cooling 30 mL methanol were added dropwise within 20 min. During this time the temperature was maintained at 10° C. to 20° C. with an ice bath. The reaction mixture was stirred for 30 min at RT and then 45 mL of a 2M aqueous hydrochloric acid solution was added dropwise thereto within 30 min. The reaction mixture was concentrated by rotary evaporation i. vac. with gentle heating. The residue was diluted with water to approx. 200 mL and extracted with 200 mL EtOAc. The aqueous phase was made alkaline with a 15% (w/v) aqueous potassium carbonate solution and continuously extracted overnight with a rotary perforator according to Ludwig (Messrs. Normag) with diethyl ether. The organic extract was evaporated to dryness by rotary evaporation.

1. temperatureThe reaction mixture was refluxed for 2 h
2. additionwere added dropwise within 20 min
3. temperatureDuring this time the temperature was maintained at 10° C. to 20° C. with an ice bath
4. waitwithin 30 min
5. concentrationThe reaction mixture was concentrated by rotary evaporation i
6. additionThe residue was diluted with water to approx. 200 mL
7. extractionextracted with 200 mL EtOAc
8. customwith a 15% (w/v) aqueous potassium carbonate solution and continuously extracted overnight
9. extractionThe organic extract
10. customwas evaporated to dryness by rotary evaporation

ORD record

ord-38cf4039429543139acddb25d6abdccf

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08829006B2