N-bromobutanimide → 6-Bromo-5-chloro-1,2,3,4-tetrahydroquinolin-2-one

HRID 1521646Notes

Reaction equation

HRID 1521646 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]2

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 190277365-chloro-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 709792116-Bromo-5-chloro-1,2,3,4-tetrahydroquinolin-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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

  1. customReaction mixture
  2. concentrationThe reaction mixture was concentrated
  3. additiondiluted with ice cold water (100 mL)
  4. stirringwith constant stirring
  5. filtrationthe solid residue was filtered
  6. customdried

Sources & evidence

ORD record
ord-0cb1670d5b674b65b076adebabadc58c
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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