Lithium Chloride → HCID 68465953, compound

Participants

Reaction Steps

A solution of 5-[3-(2-chloroethoxy)-phenyl]-1-(3,4-dimethoxybenzyl)-4-oxo-1,4-dihydro-pyridine-3-carbonitrile (2.5 g, 5.9 mmol) and LiCl (2.3 g, 53 mmol) in 22 mL of POCl3 was heated at reflux for 2.5 h. The excess POCl3 was removed by concentrating in vacuo. The residue was dissolved in 100 mL CH2Cl2 and washed with ice-cold 3 N NaOH. The organic layer was separated, dried over anhydrous MgSO4, filtered, concentrated in vacuo, and purified by flash chromatography on silica gel eluting with 30% EtOAc in hexanes to yield 1.3 g (75% yield) of 4-chloro-5-[3-(2-chloroethoxy)phenyl]nicotinonitrile as an off-white solid.

Provenance & Evidence