Phosphorus oxychloride → HCID 18315854, compound

Participants

Reaction Steps

6-Hydroxy-5-(4-methoxyphenyl)-1-methyl-3-(4-methylthiazol-2-yl)-1H-pyridin-2-one (0.13 g) was dissolved in freshly distilled POCl3 (5 cm3) under N2 and heated to reflux for 1.5 h. The excess reagent was then removed by evaporation and the residue partitioned between ethyl acetate (100 cm3) and saturated sodium bicarbonate solution (50 cm3). The aqueous layer was washed with ethyl acetate (2×100 cm3) and the combined organic phase dried (MgSO4) and evaporated. Purification on silica gel eluting with ethyl acetate-hexane mixtures afforded 6-chloro-5-(4-methoxyphenyl)-1-methyl-3-(4-methylthiazol-2-yl)-1H-pyridin-2-one as a yellow powder. δH (250 MHz; CDCl3); 2.49 (3H, s), 3.86 (3H, s), 3.93 (3H, s), 6.96 (2H, d, J 8.7 Hz), 7.01 (1H, s) 7.33 (2H, d, J 8.7 Hz) and 8.60 (1H, s).

Provenance & Evidence