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

HRID 1296136Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1296136
[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-68a4bd1a5cac476c8895a8165f78e9d0
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07244725B2

Notizen zur Reaktion

Wird geladen…