Ammonia → HCID 178428602, compound

Participants

Reaction Steps

A solution of 4-methyl-pyridin-2-ol V-a (25 g, 229 mmol) in glacial acetic acid (350 mL) and EtOAc (680 mL) was treated with NBS (37.4 g, 210 mmol) and stirred at room temperature for 30 min. The mixture was then taken to pH 8 with aqueous ammonia and extracted with EtOAc. The separated organics were washed with 1:1 H2O/brine then dried (MgSO4), filtered and evaporated before purification by silica column chromatography (1-4% EtOH/DCM) to afford the desired product V-b as a white solid (8.66 g). 1H NMR (300 MHz, DMSO) δ 11.90 (s, 1H), 7.32 (d, J=6.6 Hz, 1H), 6.19 (d, J=6.6 Hz, 1H), 2.25 (s, 3H).

Provenance & Evidence