Bromine → 6-Bromo-3,4-dihydro-4-methyl-2(1H)-quinolinone
Reaction equation
[Br:1]Br.[CH3:3][CH:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6](=[O:14])[CH2:5]1>C(O)(=O)C>[Br:1][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:14])[CH2:5][CH:4]2[CH3:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of bromine (0.08 cm3) in acetic acid (1 cm3) was added at room temperature to a stirred solution of 4-methyl-3,4-dihydro-2-(1H)-quinolone (0.5 g) in acetic acid (4.0 cm3). After 2 hours, volatile material was removed in vacuo, the residue was partitioned between chloroform (50 cm3) and water (20 cm3), and the organic phase was further extracted with chloroform (2×20 cm3). The combined and dried (MgSO4) organic extracts were evaporated in vacuo and the solid residue was recrystallised from ethyl acetate to afford 6-bromo-4-methyl-3,4-dihydro-2-(1H)-quinolone, m.p. 190°, (0.35 g).