Diisopropylamine → HCID 15631335, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1.10 ml (7.88 mmol) of diisopropylamine in 20 ml of tetrahydrofuran at 0° C. under argon was added 4.1 ml (6.23 mmol) of 1.52M n-butyl lithium in hexanes dropwise. To the lithium diisopropylamide solution was added 502.0 mg (3.15 mmol) of 4-methyl-8-quinolinol (see example 1A) in 10 ml of tetrahydrofuran over 15 minutes at 0° C. The dark solution, which contained some insoluble material, was allowed to stir for five hours at 0° C., cooled to -78° C. and 0.46 ml (3.31 mmol) of 1-bromohexane was added. After 30 minutes at -78° C., the reaction was allowed to warm gradually from -30° C. to room temperature over 1.5 hours. The solution was allowed to stir for 45 minutes at room temperature, quenched with pH 6.5 phosphate buffer and extracted with ether. The ether extract was washed with water and brine, dried (magnesium sulfate) and evaporated to afford 757 mg of a yellow-brown solid. This material was dissolved in hot hexane, filtered to remove an insoluble residue and the filtrate was evaporated. Recrystallization from heptane provided 511.7 mg of the title compound as yellow plates: melting point 92°-93.5° C.

Provenance & Evidence