HCID 19612101, compound → HCID 15869798, compound

1.23 g (3.8 mmol) of 1-(3-chloropropionyl)indoline-6-diazonium tetrafluoroborate [prepared as described in step (1) above] were suspended in 20 ml of heptane, and the suspension was heated under reflux for 1 hour. At the end of this time, the mixture was cooled to room temperature, and the reaction product was poured into ice. The mixture was then extracted with 50 ml of ethyl acetate, and the organic extract was washed with 50 ml of water, after which it was dried over anhydrous magnesium sulfate. The mixture was filtered, and then 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 810 mg (3.6 mmol) of the title compound (yield: 95%).

1. temperaturethe suspension was heated
2. temperatureunder reflux for 1 hour
3. additionthe reaction product was poured into ice
4. extractionThe mixture was then 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 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-0a0b516f489d403c88afe803dbcfbc0d

Source dataset

uspto-grants-1999_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05981752