HCID 19612101, compound → HCID 15869798, compound

1.20 g (3.7 mmol) of 1-(3-chloropropionyl)indoline-6-diazonium tetrafluoroborate [prepared as described in step (1) above] was suspended in 2 ml of heptane, and the suspension was heated under reflux for 2 hours. After the resulting mixture had cooled to room temperature, the reaction product was poured into ice, and the mixture was extracted with 50 ml of ethyl acetate. The organic extract was washed with 50 ml of water, after which it was dried over anhydrous magnesium sulfate. The mixture was then filtered, and the solvent was removed from the filtrate by distillation under reduced pressure. 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 710 mg (3.1 mmol) of the title compound (yield: 84%).

1. temperaturethe suspension was heated
2. temperatureunder reflux for 2 hours
3. additionthe reaction product was poured into ice
4. extractionthe mixture was extracted with 50 ml of ethyl acetate
5. extractionThe organic extract
6. washwas washed with 50 ml of water
7. dry with materialafter which it was dried over anhydrous magnesium sulfate
8. filtrationThe mixture was then filtered
9. customthe solvent was removed from the filtrate by distillation under reduced pressure
10. customThe resulting residue was purified by silica gel column chromatography
11. additionby volume mixture of hexane and ethyl acetate as the eluent

ORD record

ord-bc9ea64ba4cc41959d8f7e6ee4a3566b

Source dataset

uspto-grants-1999_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05981752