Nitric Acid → HCID 20094336, compound

Participants

Reaction Steps

To a solution of 1-acetyl-5-(2-bromopropyl)indoline (153 g) in acetic acid (240 ml) was added fuming nitric acid (120 ml) with stirring under ice cooling over a period of 1 hour, and the mixture was stirred at room temperature for 30 minutes. After the reaction mixture was poured into ice water slowly, the precipitates were collected by filtration, and dissolved in benzene (1.5 l). The benzene solution was washed with water, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was recrystallized from ethyl acetate-isopropyl ether to give 155 g of 1-acetyl-5-(2-bromopropyl)-7-nitroindoline melting at 119°-120° C.

Provenance & Evidence