N-bromobutanimide → 6-bromo-5-cyclopropyl-3,4-dihydroquinolin-2(1H)-one
Reaction equation
[CH:1]1([C:4]2[CH:13]=[CH:12][CH:11]=[C:10]3[C:5]=2[CH2:6][CH2:7][C:8](=[O:14])[NH:9]3)[CH2:3][CH2:2]1.[Br:15]N1C(=O)CCC1=O>CN(C)C=O>[Br:15][C:13]1[C:4]([CH:1]2[CH2:3][CH2:2]2)=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:14])[CH2:7][CH2:6]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of 5-cyclopropyl-3,4-dihydroquinolin-2(1H)-one (147-5; 0.5 g, 0.00267 mol) in N,N-dimethylformamide (10 mL) was added N-bromosuccinimide (0.47 g, 0.0026 mol) portion wise at 0° C. Reaction mixture was allowed to stir at room temperature for 4 h. The reaction mixture was concentrated and diluted with ice cold water (100 mL) with constant stirring, the solid residue obtained was filtered and dried to obtain the title compound. MS (M+1): 266.1.