N-bromobutanimide → 6-Bromo-5-chloro-1,2,3,4-tetrahydroquinolin-2-one
Reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][C:6](=[O:12])[NH:7]2.[Br:13]N1C(=O)CCC1=O>CN(C)C=O>[Br:13][C:11]1[C:2]([Cl:1])=[C:3]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:12])[CH2:5][CH2:4]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of 5-chloro-3,4-dihydroquinolin-2(1H)-one (143-4; 0.4 g, 0.022 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 12 h. The reaction mixture was concentrated and diluted with ice cold water (100 mL) with constant stirring and the solid residue was filtered and dried to obtain the title compound. MS (M+1): 259.9.
Workup
- customReaction mixture
- concentrationThe reaction mixture was concentrated
- additiondiluted with ice cold water (100 mL)
- stirringwith constant stirring
- filtrationthe solid residue was filtered
- customdried
Sources & evidence
- ORD record
- ord-0cb1670d5b674b65b076adebabadc58c
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09073929B2
Reaction notes
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