Dimethylformamide → 6-Chloro-3-pyridinecarbonitrile

Participants

Reaction Conditions

Reaction Steps

Oxalyl chloride (40 mL) was added dropwise at 0° C. to a suspension of 6-chloropyridine-3-carboxylic acid (18 g, 114 mmol) in 300 mL of DCM with 3 mL of DMF. The mixture was stirred at 25° C. for 2 hours and the clear solution was concentrated to dryness under reduced pressure. The residue was dissolved in 100 mL of anhydrous acetonitrile and then added to 500 mL of diluted aqueous NH3.H2O at 0° C. The mixture was stirred for 30 minutes then extracted with EtOAc twice. The combined EtOAc layers were washed with water and brine, dried over anhydrous Na2SO4 and concentrated. The residue was dissolved in 100 mL of DMF and cooled to 0° C. with ice/water bath. Cyanuric chloride (21.2 g, 114.9 mmol) was added and the mixture was stirred for 2 hours at 0° C. and then poured into ice/water. The resulting solid was collected by filtration, washed with water, dissolved in DCM, dried over anhydrous Na2SO4 and concentrated to afford 6-Chloropyridine-3-carbonitrile.

Provenance & Evidence