Nitrogen → 4,6-Dimethyl-3-bromo-5-benzyl-1h-pyridin-2-one
Reaction equation
[CH3:1][C:2]1[C:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:6]([CH3:15])[NH:5][C:4](=[O:16])[CH:3]=1.[Br:17]Br.N#N>C(O)(=O)C>[CH3:1][C:2]1[C:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:6]([CH3:15])[NH:5][C:4](=[O:16])[C:3]=1[Br:17]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 4,6-dimethyl-5-benzyl-1H-pyridin-2-one (2.21 g, 10.4 mmol) in anhydrous acetic acid (10 mL) was added bromine (3.3 g, 1.06 mL, 20.7 mL). It was stirred at room temperature for one hour. Then the reaction vessel was blew N2 to remove bromine and evaporation removed volatiles. The residue was partitioned between CH2Cl2/sat. NaHCO3/saline (100/50/50 mL). The organic layer was dried over Na2SO4 and evaporation gave the brominated compound as a yellow solid (3.17 g, 100%). 1H NMR (CDCl3) δ 2.07 (s, 3H), 2.37 (s, 3H), 3.81 (s, 2H), 7.00–7.40 (m, 5H); MS (CI) m/z 293, 295 (MH+).