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

HRID 525879노트

반응식

HRID 525879 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-978ea30d805445d69b34229006f0ffd0
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340556B2

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