Aluminum(III) Chloride → HCID 69217133, compound

Participants

Reaction Steps

A solution of 2-[3-(3-methyl-but-2-enoylamino)-phenyl]-heptanoic acid ethyl ester (3.822 g, 11.5 mmole) in 60 mL of dichloromethane was treated with 4.613 g of aluminum chloride and heated at reflux for four hours. The reaction mixture was poured onto 200 mL of ice-water and extracted with two 100 mL portions of dichloromethane. The combined organic extracts were washed with 200 mL of saturated aqueous sodium bicarbonate solution. The organic phase was dried over MgSO4, filtered and concentrated in vacuo to give a yellow oil. The product was purified by flash chromatography (SiO2, 25% ethyl acetate in hexanes) to yield 3.657 g of 2-(4,4-dimethyl-2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl)-heptanoic acid ethyl ester as a pale yellow oil.

Provenance & Evidence