1,2-Dichlorobenzene → HCID 15869798, compound

Temperature

10 °C

260 mg (2.2 mmol) of 6-amino-1-(3-chloropropionyl)indoline (prepared as described in Preparation 6) were dissolved in 10 ml of methylene chloride, and 450 mg (2.0 mmol) of nitrosonium tetrafluoroborate were added to the resulting solution while ice-cooling so that the internal temperature was maintained at 10° C. or lower. The mixture was then stirred while ice-cooling for 30 minutes. At the end of this time, 10 ml of 1,2-dichlorobenzene were added to the mixture, and the mixture was stirred at 90° C. for 1 hour. The solvent was then removed from the reaction mixture by distillation under reduced pressure and the resulting residue was purified by silica gel column chromatography, using a 4:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 97 mg (0.39 mmol) of the title compound as crystals (yield: 20%).

1. temperaturecooling so that the internal temperature
2. temperaturecooling for 30 minutes
3. stirringthe mixture was stirred at 90° C. for 1 hour
4. customThe solvent was then removed from the reaction mixture by distillation under reduced pressure
5. customthe resulting residue was purified by silica gel column chromatography
6. additionby volume mixture of hexane and ethyl acetate as the eluent

ORD record

ord-ab8539beb2f6423c97d49b6a6a555f70

Source dataset

uspto-grants-1999_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05981752