Hydrazine hydrate (1:1) → 1-Aminopropyl-3-phenyl-5-chloroindazole

Participants

Reaction Steps

1-Phthalimidopropyl-3-phenyl-5-chloroindazole (8.3 g) and hydrazine hydrate (2.0 g) were added to ethanol (150 ml) followed by heating under reflux for 3 hours. The reaction mixture was concentrated under reduced pressure and to the residue were added benzene (150 ml) and 10% aqueous sodium hydroxide solution (200 ml) followed by stirring at room temperature for 1 hour. The organic layer was separated from the mixture and it was washed with water, dried over sodium sulfate and concentrated under reduced pressure to obtain 5.5 g of 1-aminopropyl-3-phenyl-5-chloroindazole as an oily product. The product was treated with ether-hydrochloric acid to form its hydrochloride. After recrystallization from ethanol-ether, the product had a melting point between 163°-164° C.

Provenance & Evidence