Hydrochloric Acid → 1-(8-Quinolyl)indene

Participants

Reaction Conditions

Reaction Steps

30 8-bromoquinoline (10.4 g, 50 mmol) was first placed in 100 ml of THF and cooled to approximately −100° C. 20 ml of n-BuLi (2.5 M in hexane, 50 mmol) were added dropwise, and the internal temperature was kept below −80° C. After the addition was ended, stirring was continued for a further 15 minutes at −80° C., and then 6.6 g of 1-indanone (50 mmol), dissolved in 30 ml of THF, were added dropwise. The reaction mixture was then allowed to return to room temperature slowly and then heated for three hours. in reflux. Once the mixture had cooled to room temperature, first ice and then hydrochloric acid was added to approximately pH 1, and the mixture was stirred for 30 minutes. The aqueous and organic phases were separated; the aqueous phase was mixed with ammonia solution to a pH of approximately 9 and extracted with ether, and the combined organic phases were then concentrated until dry in a vacuum. The thus-obtained viscous oil (1-(8-quinolyl)-indan-1-ol (8H2O)) was mixed with hydrochloric acid until the pH was 0, heated for two hours in reflux, and then neutralized. After processing and drying, 6.6 g of 1-(8-quinolyl)indene (55%) were obtained in the form of a colorless solid.

Provenance & Evidence