Potassium Cyanide → 3,4-dihydro-2H-pyrano[2,3-b]pyridine-4-carbonitrile

Participants

Reaction Conditions

Reaction Steps

To a mixture of 4-chloro-3,4-dihydro-2H-pyrano[2,3-b]pyridine (18.7 mmol) in 60 mL DMF was added KCN (56.1 mmol) and the mixture was stirred at 90° C. overnight. After cooling to RT, the mixture was diluted with aq. 0.5 M NaOH solution and extracted 3 times with EtOAc. The combined organic layers were washed again with aq. 0.5 M NaOH solution and once with brine. The organic phase was dried over MgSO4 and concentrated in vacuo. Purification with CC (KP-SIL™ from Biotage) using Hept/EtOAc (4/1) to EtOAc gives the desired compound as yellow oil.

Provenance & Evidence