Chlorosuccinimide → 6-Chloro-5-hydroxynicotinonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-hydroxy-nicotinonitrile (2.0 g, 16.66 mmol), and N-chlorosuccinimide (3.3 g, 25.0 mmol) in acetonitrile (33 mL) was heated in a sealed tube at 107° C. overnight. Acetonitrile was removed under reduced pressure, the residue was diluted with EtOAc (100 mL). The organic layer was washed with water (10 mL) and brine (2×10 mL), dried over Na2SO4, filtered, and concentrated to give brown oil. Purification was accomplished by flash chromatography on silica gel using 20-80% EtOAc/hexanes gradient elution to yield the title compound (0.55 g, 36%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.70 (s, 1 H), 8.35 (d, J=2.0 Hz, 1 H), 7.67 (d, J=2.0 Hz, 1 H); MS (ES) m/z: 153 (M−1)−.

Provenance & Evidence