Hydrochloric Acid → 2,3-dihydro-1H-indol-7-yl(phenyl)methanone

Temperature

160 °C

To a solution of 357 mg (3 mmol) of indoline 3 dissolved in 10 ml of 1,2-dichloroethane are added 0.5 ml (3×1.2 mmol) of triethylamine, 0.44 ml (3×1.2 mmol) of boron trifluoride ether adduct, and 0.43 ml (3×1.2 mmol) of silicon tetrachloride, and the mixture is heated under reflux with stirring for 2 hours. The reaction mixture is evaporated; 0.62 ml (3×2 mmol) of benzonitrile is added to the residue and the mixture is heated at 160° C. with stirring for 5 hours and then cooled. The mixture is mixed with 5 ml of 6N hydrochloric acid and heated at 100° C. for 20 minutes. The reaction mixture is basified with potassium carbonate and extracted with dichloromethane. The organic layer is washed with water, dried over anhydrous potassium carbonate, and concentrated. The residue is chromatographed on a column of 4.6 g of silica-gel and eluted with dichloromethane. The eluate from dichloromethane is concentrated. The residue is recrystallized from ether-petroleum either to give 555 mg of 7-benzoylindoline 7 as crystals.

1. temperaturethe mixture is heated
2. temperatureunder reflux
3. customThe reaction mixture is evaporated
4. stirringwith stirring for 5 hours
5. temperaturecooled
6. temperatureheated at 100° C. for 20 minutes
7. extractionextracted with dichloromethane
8. washThe organic layer is washed with water
9. dry with materialdried over anhydrous potassium carbonate
10. concentrationconcentrated
11. customThe residue is chromatographed on a column of 4.6 g of silica-gel
12. washeluted with dichloromethane
13. concentrationThe eluate from dichloromethane is concentrated
14. customThe residue is recrystallized from ether-petroleum

ORD record

ord-c9d384bbd3c1454ba61129582eb221de

Source dataset

uspto-grants-1989_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04831132