Chlorosuccinimide → 6-Bromo-8-chloro-3,4-dihydroquinolin-2(1H)-one

HRID 1521669Notes

Reaction equation

HRID 1521669 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1F)[NH:8][C:7](=[O:13])[CH2:6][CH2:5]2.[Cl:14]N1C(=O)CCC1=O>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:14])[CH:11]=1)[NH:8][C:7](=[O:13])[CH2:6][CH2:5]2

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 434576896-bromo-7-fluoro-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 709797726-Bromo-8-chloro-3,4-dihydroquinolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 6-bromo-7-fluoro-3,4-dihydroquinolin-2(1H)-one (122-3; 3 g, 0.0012 mol) in N,N-dimethylformamide (30 mL) was added N-chlorosuccinimide in N,N-dimethylformamide (3 mL) (1.4 g, 0.0105 mol) at 70° C. drop wise over a period of 2 h. Reaction mass was allowed to stir at 70° C. for 14 h. The reaction mixture was cooled and diluted with ice cold water. The precipitated solid was filtered and dried to obtain title compound. MS (M−1): 278.12.

Workup

  1. customReaction mass
  2. temperatureThe reaction mixture was cooled
  3. additiondiluted with ice cold water
  4. filtrationThe precipitated solid was filtered
  5. customdried

Sources & evidence

ORD record
ord-579011f185ae494ea6a7e348b3587f07
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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