N-bromobutanimide → HCID 22677333, compound

Participants

Reaction Steps

N-Bromosuccinimide (0.377 g, 2.13 mmol) was added all at once to a solution of methyl 4-acetamido-3-chloro-6-(1-ethoxyvinyl)pyridine-2-carboxylate (0.636 g, 2.13 mmol) in THF (40 mL) and water (2 mL) at room temperature. After 15 minutes, the reaction mixture was concentrated and the residue partitioned between dichloromethane and water. The organic layer was separated, dried (MgSO4), and concentrated to provide methyl 4-acetamido-3-chloro-6-(bromoacetyl)pyridine-2-carboxylate (0.714 g, 2.04 mmol). 1H NMR (CDCl3): δ 9.12 (s, 1H), 7.99 (br.s, 1H), 4.82 (s, 2H), 4.06 (s, 3H), 2.36 (s, 3H).

Provenance & Evidence