Water → 4,4-Dimethyl-1,2,3,4-tetrahydroquinoline

Participants

Reaction Conditions

Reaction Steps

To 4,4-dimethyl-3,4-dihydro-1H-quinolin-2-one (7.6 g, 43 mmol) in THF (100 mL), was added lithium aluminum hydride (5 g, 134 mmole) portion wise with ice bath. The reaction mixture was warmed to 50° C. and stirred overnight. The reaction mixture was cooled to rt and treated with water (5 mL), 10% sodium hydroxide aqueous solution (5 mL) and water (15 mL). The resulting mixture was stirred for another 10 minutes. The mixture was filtered through Celite and the Celite was washed with ethyl acetate to a volume of approximately 50 mL. The resulting ethyl acetate solution was washed with brine (50 mL×2) and dried over MgSO4. Concentration of the filtrate and purification by silica gel column chromatography eluting with hexane/ethyl acetate (9/1) yielded 4,4-dimethyl-1,2,3,4-tetrahydro-quinoline 2-1 as a brown oil (6.0 g, 87% yield). MS: 162.0 (M+H)+; tR=1.47 min (method 1).

Provenance & Evidence