N-bromobutanimide → 5-bromo-3-ethyl-6-methyl-1H-pyridin-2-one

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Reaction Steps

A 2 neck round bottom flask, equipped with an overhead stirrer is charged with 3-ethyl-6-methyl-1H-pyridin-2-one (33.45 g, 0.26 mol) obtained from Step 1 as described above, N-bromosuccinimide (48.6 g, 0.273 mol) and methanol (867 mL) and the mixture stirred at ambient temperature for 17 hr. The mixture is then concentrated to a volume of 200 mL, diluted with water (600 mL) and the resulting suspension is chilled in an ice bath. The solids are collected by filtration, washed with water (300 mL) and dried in a vacuum oven at 64° C. for 24 hr to afford 5-bromo-3-ethyl-6-methyl-1H-pyridin-2-one (53.56 g, 95.3% yield) as an off white solid. LC/MS: MS m/e=215/217 (M+H), RT 2.64 min.

Provenance & Evidence