Potassium Iodide → tert-butyl N-[6-[[(Z)-[cyano(phenyl)methylidene]amino]oxymethyl]-2-pyridinyl]carbamate

Participants

Reaction Steps

To a solution of (2Z)-(hydroxyimino)(phenyl)acetonitrile (2.5 g, 17.10 mmol, 1 eq.) in 100 ml of acetonitrile and 10 ml DMF was added tert-butyl [6-(chloromethyl)pyridin-2-yl]carbamate (4.15 g, 17.10 mmol, 1 eq.) followed by potassium iodide (283 mg, 1.71 mmol, 0.1 eq.) and caesium carbonate (8.36 g, 25.65 mmol, 1.5 eq.). The reaction was stirred overnight at room temperature. The solvent was then evaporated and the residue dissolved in EtOAc (100 ml). The organic layer was washed with H2O and dried over MgSO4 then concentrated. tert-butyl {6-[({[(Z)-cyano(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate (5.39 g, 80% yield, only 1 oxime isomer) was obtained as a white solid.

Provenance & Evidence