N-bromobutanimide → 6-Bromo-1,2,3,4-tetrahydroquinolin-4-one

HRID 1991549노트

반응식

HRID 1991549 반응식
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH2:3][CH2:2]1.[Br:12]N1C(=O)CCC1=O>ClCCl>[Br:12][C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[NH:1][CH2:2][CH2:3][C:4]2=[O:11]

참가 물질

4

반응물 2

HCID 67184N-bromobutanimideHCID 1171582,3-dihydroquinolin-4(1H)-one

생성물 1

HCID 7594476-Bromo-1,2,3,4-tetrahydroquinolin-4-one수율 91.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 2,3-dihydroquinolin-4(1H)-one (2.94 g) in dichloromethane (25 mL) was added N-bromosuccinimide (3.63 g). The mixture was stirred at room temperature for 1.5 h and was partitioned between aqueous sodium bicarbonate and dichloromethane. The organic layer was washed with brine, dried with sodium sulfate, filtered, and concentrated. The concentrate was chromatographed on silica gel using a 35% ethyl acetate in heptane solvent solution and gave 4.14 g of the title compound. MS (ESI−) for C9H8BrNO m/z 225.77 (M−H)−.

후처리

  1. customwas partitioned between aqueous sodium bicarbonate and dichloromethane
  2. washThe organic layer was washed with brine
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe concentrate was chromatographed on silica gel using a 35% ethyl acetate in heptane solvent solution

출처 및 근거

ORD 기록
ord-be81e53f22d045899e33d850127c699f
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07645780B2

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