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

Participants

Reaction Steps

To a refluxing suspension of 10 g (0.26 mol) of lithium aluminum hydride in 100 ml of ether was added dropwise over a period of 1 hour a solution of 21.0 g (0.21 mol) of 4,4-dimethyl-2-oxo-1,2,3,4-tetrahydroquinoline in 200 ml of ether-tetrahydrofuran (2:1, volume per volume). Refluxing was continued for 16 hours, and then to the cooled reaction mixture was added 50 ml of water and 50 ml of 10% sodium hydroxide. The aqueous phase was extracted with ether, and the combined ether extracts were dried (MgSO4) and evaporated in vacuo to give 17.2 g (89% yield) of the title compound as a clear oil.

Provenance & Evidence