2-Hydroxyquinoline → 1-(3-chloropropyl)quinolin-2(1H)-one

HRID 1191383노트

반응식

HRID 1191383 반응식
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]1=[O:11].CN(C=O)C.[H-].[Na+].Br[CH2:20][CH2:21][CH2:22][Cl:23]>CCOC(C)=O>[Cl:23][CH2:22][CH2:21][CH2:20][N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]1=[O:11]

참가 물질

6

반응물 4

HCID 60382-HydroxyquinolineHCID 6228DimethylformamideHCID 80061-Bromo-3-chloropropaneHCID 24758Sodium hydride

생성물 1

HCID 193797261-(3-chloropropyl)quinolin-2(1H)-one수율 41%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

A 7 mL vial was charged with 1H-quinolin-2-one (0.62 g, 4.2 mmol), 4 mL dry DMF and NaH (60% in oil, 0.200 g, 5.1 mmol). The mixture was stirred under a N2 atmosphere at rt for 45 min, and thereafter 1-bromo-3-chloropropane (0.42 mL, 4.2 mmol) was added and the reaction was stirred at rt overnight. The reaction was diluted with EtOAc (50 mL) and washed with water (15 mL). The water phase was extracted with EtOAc (25 mL) and the combined organic phase was dried (Na2SO4), filtered, concentrated under reduced pressure and the residue was purified by flash chromatography (SiO2; CH2Cl2) to yield the title compound (0.38 g, 41%), containing 15% of 1-(3-bromopropyl)-1H-quinolin-2-one. 1H NMR (CD3OD) δ 7.90 (d, J=9.4 Hz, 1H), 7.73-7.57 (m, 3H), 7.34-7.28 (m, 1H), 6.66 (d, J=9.4 Hz), 4.46 (t, J=7.4 Hz, 2H), 3.71 (t, J=6.4 Hz, 2H), 2.21-2.02 (m, 2H); 13C NMR (CD3OD) δ 163.2, 140.7, 138.8, 131.3, 129.3, 122.8, 121.4, 120.2, 114.4, 42.18, 40.2, 30.5.

후처리

  1. stirringthe reaction was stirred at rt overnight
  2. washwashed with water (15 mL)
  3. extractionThe water phase was extracted with EtOAc (25 mL)
  4. dry with materialthe combined organic phase was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customthe residue was purified by flash chromatography (SiO2; CH2Cl2)

출처 및 근거

ORD 기록
ord-189add6e824f46e7a41d8ac326efabd2
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680115B2

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