Dimethylformamide → 4-Chloropyridine-3-carbaldehyde

Participants

Reaction Steps

A solution (50 ml) of 4-chloropyridine (25.0 g, 0.22 mol) in tetrahydrofuran was added dropwise to a tetrahydrofuran solution (300 ml) of lithium diisopropylamide prepared from a solution (179 ml, 0.29 mol) of 1.6 M n-butyllithium in hexane and diisopropylamine (33.4 g, 0.33 mol) under an argon atmosphere at −78° C. After stirring for 30 min., DMF (19.3 g, 0.26 mol) was added and the mixture was gradually heated to room temperature. The reaction mixture was extracted with ethyl acetate (200 ml)-5% NH4Cl aq. (300 ml). The organic layer was dried (MgSO4) and the solvent was evaporated under reduced pressure to give a crude title compound (27 g, 86%) as an oil.

Provenance & Evidence