1-Bromo-3-chloropropane → 1-(3-Chloropropyl)-6-methyl-3,4-dihydro-1H-quinolin-2-one

HRID 969348노트

반응식

HRID 969348 반응식
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2.[H-].[Na+].Br[CH2:16][CH2:17][CH2:18][Cl:19]>CN(C=O)C>[Cl:19][CH2:18][CH2:17][CH2:16][N:8]1[C:9]2[C:4](=[CH:3][C:2]([CH3:1])=[CH:11][CH:10]=2)[CH2:5][CH2:6][C:7]1=[O:12]

참가 물질

5

반응물 3

HCID 80061-Bromo-3-chloropropaneHCID 24758Sodium hydrideHCID 152705756-Methyl-3,4-dihydroquinolin-2(1H)-one

생성물 1

HCID 179560711-(3-Chloropropyl)-6-methyl-3,4-dihydro-1H-quinolin-2-one수율 87.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A reaction flask was charged with 6-methyl-3,4-dihydro-1H-quinolin-2-one (107LH05) (0.300 g, 1.26 mmol) in dry DMF (5 mL) under Argon. NaH (60% in oil, 0.055 g, 1.38 mmol) was added and the mixture was stirred at rt for 1 h. Then 1-bromo-3-chloropropane (0.198 g, 1.24 mmol) was added followed by stirring at rt for 20 h. The reaction mixture was quenched with water, and the product extracted into EtOAc. The combined organic layers were dried over Na2SO4, filtered, and concentrated. The crude product was purified by flash CC (SiO2; DCM) to give the crude title compound (107LH14) (0.257 g).

후처리

  1. stirringby stirring at rt for 20 h
  2. customThe reaction mixture was quenched with water
  3. extractionthe product extracted into EtOAc
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by flash CC (SiO2; DCM)

출처 및 근거

ORD 기록
ord-002f2062ccd248ffb3e890855576d938
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07307075B2

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