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

HRID 1991549Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1991549
[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]

Komponenten

4

Edukt 2

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

Produkt 1

HCID 7594476-Bromo-1,2,3,4-tetrahydroquinolin-4-oneAusbeute 91,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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)−.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-be81e53f22d045899e33d850127c699f
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07645780B2

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