m-Chloroperbenzoic acid → 8-Bromo-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl acetate

HRID 525879Notes

Reaction equation

HRID 525879 reaction equation
C([C:4]1[C:13](=[O:14])[C:12]2[C:7](=[C:8]([Br:15])[CH:9]=[CH:10][CH:11]=2)[N:6]([CH3:16])[CH:5]=1)(=O)C.C1C=C(Cl)C=[C:19]([C:24]([O:26]O)=[O:25])C=1>ClCCl>[C:24]([O:26][C:4]1[C:13](=[O:14])[C:12]2[C:7](=[C:8]([Br:15])[CH:9]=[CH:10][CH:11]=2)[N:6]([CH3:16])[CH:5]=1)(=[O:25])[CH3:19]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 867327443-acetyl-8-bromo-1-methylquinolin-4(1H)-one

Product 1

HCID 867327468-Bromo-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl acetateYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-acetyl-8-bromo-1-methylquinolin-4(1H)-one (3.4 g, 12.14 mmol) in dichloromethane (60 mL) at room temperature was added portionwise with stirring m-CPBA (4.08 g, 18.21 mmol). The resulting mixture was stirred at room temperature for 1 h. The excess m-CPBA was quenched via addition of 15% aqueous Na2SO3 (30 mL), and the resulting mixture was stirred at room temperature for 0.5 h. The layers were separated, and the organic layer was washed sequentially with water (100 mL), 5% aqueous NaHCO3 (100 mL), and brine (100 mL). The organic layer was dried (Na2SO4), filtered, and concentrated in vacuo to afford crude 8-bromo-1-methyl-4-oxo-1,4-dihydroquinolin-3-yl acetate (3.68 g, 10.56 mmol, 87% yield) as brown solid, which was used in the next hydrolysis step without further purification. LCMS: (M+H)+: 295.9.

Workup

  1. customThe excess m-CPBA was quenched via addition of 15% aqueous Na2SO3 (30 mL)
  2. stirringthe resulting mixture was stirred at room temperature for 0.5 h
  3. customThe layers were separated
  4. washthe organic layer was washed sequentially with water (100 mL), 5% aqueous NaHCO3 (100 mL), and brine (100 mL)
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-978ea30d805445d69b34229006f0ffd0
Source dataset
uspto-grants-2016_05
Patent number
US09340556B2

Reaction notes

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