N-bromobutanimide → 5-Bromo-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

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Reaction Steps

A mixture of 6-methyl-2-oxo-1,2-dihydro-3-pyridinecarbonitrile (26.23 g, 95.5 mmol) and N-bromosuccinimide (36.54 g, 205 mmol) in 1,2-dichloroethane (500 mL) heated to reflux for 18 hours, cooled to room temperature, and filtered. The solid was treated with water (1 L), stirred for 2 hours, filtered, washed with water, and dried under vacuum to provide 36.85 g (88%) of the desired product of sufficient purity for subsequent use. MS (DCI/NH3) m/z 230 (M+NH4)+; 1H NMR (DMSO-d6) δ 12.96 (br s, 1H), 8.34 (s, 1H),2.36 (s, 3H).

Provenance & Evidence