HCID 19612101, compound → HCID 15869798, compound

Participants

Reaction Steps

320 mg of crude 1-(3-chloropropionyl)indoline-6-diazonium tetrafluoroborate [prepared as described in step (1) above] were suspended in 10 ml of heptane, and the suspension was heated under reflux for 1 hour. The resulting mixture was cooled to room temperature, and then the reaction product was poured into ice, extracted with 50 ml of ethyl acetate and washed with 50 ml of water, after which it was dried over anhydrous magnesium sulfate. The mixture was 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 70 mg (0.31 mmol) of the title compound (yield: 40% in two steps).

Provenance & Evidence