Ammonia → 1-(8-Quinolyl)-2-methylindene

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

6.70 ml of n-BuLi (16.8 mmol) was added dropwise at 100° C. to a solution of 3.50 g of o-bromoquinoline (16.8 mmol) in 50 ml of THF, and the mixture was stirred for 15 minutes at 80° C. Next, a solution of 50 ml of THF and 2.45 g of 2- methyl-1-indanone (16.8 mmol) was added within ten minutes to the lithiated bromoquinoline. The solution was left to return to room temperature, and subsequently boiled for three hours in reflux. After cooling to room temperature, ice was added and the mixture was acidified to pH 1 with hydrochloric acid, and subsequently heated under relfux for three hours. The reaction mixture was adjusted with ammonia solution to pH 9, and the aqueous phase was extracted with diethyl ether. The combined organic phases were dried, and the solvent was removed. The raw product was purified by distillation in a vacuum at 150 to 160° C. and 10−2 mbar. 1.5 g of 1-(8-quinolyl)-2-methylindene (45%) were obtained in the form of a viscous yellow resin.

Herkunft & Nachweise