N-bromobutanimide → 6-Bromo-7-chloro-3,4-dihydroquinolin-2(1H)-one

HRID 1521634Notes

Reaction equation

HRID 1521634 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1.[Br:13]N1C(=O)CCC1=O>CN(C)C=O.O>[Br:13][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[Cl:1])[NH:9][C:8](=[O:12])[CH2:7][CH2:6]2

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 136907667-Chloro-1,2,3,4-tetrahydroquinolin-2-one

Product 1

HCID 709793626-Bromo-7-chloro-3,4-dihydroquinolin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To solution of 7-chloro-3,4-dihydroquinolin-2(1H)-one (110-1; 2.92 g, 0.016 mol) in N,N-dimethylformamide (30 mL), was added N-bromosuccinimide (3.14 g, 0.0176 mol) portion-wise at room temperature. The resulting mixture was stirred at room temperature for 16 h. After 16 h, the reaction mixture was diluted with cold water, solid get precipitated, filtered the solid, washed the solid with water and dried under reduced pressure to afford the compound. 1H NMR (400 MHz, DMSO-d6) δ 10.20 (s, 1H), 7.56 (s, 1H), 7.01 (s, 1H), 2.87-2.84 (t, J=7.2 Hz, 2H), 2.45-2.41 (t, J=7.6 Hz, 2H); MS (M+1): 259.9.

Workup

  1. waitAfter 16 h
  2. customget
  3. customprecipitated
  4. filtrationfiltered the solid
  5. washwashed the solid with water
  6. customdried under reduced pressure
  7. customto afford the compound

Sources & evidence

ORD record
ord-8aac3e6e34024d9b9bf1ee8015a14ba5
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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