2,8-Dimethylquinoline → HCID 86707438, Verbindung

HRID 338896Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 338896
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([CH3:12])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[Br:13]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:13][CH2:12][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[N:3]=[C:2]([CH3:1])[CH:11]=[CH:10]2

Komponenten

5

Edukt 2

HCID 151012,8-DimethylquinolineHCID 67184N-bromobutanimide

Produkt 1

HCID 86707438HCID 86707438, VerbindungAusbeute 33,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 7187Benzoyl PeroxideKatalysatorHCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

To a solution of 2,8-dimethylquinoline (3.00 g, 19.1 mmol) in carbon tetrachloride (50 mL) were added benzoyl peroxide (0.0139 g, 0.057 mmol) and N-bromosuccinimide (3.57 g, 20.0 mmol). The reaction mixture was heated at reflux for 18 hours. The solid was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was dissolved in DCM (100 mL), washed with saturated sodium bicarbonate and brine, dried (sodium sulfate), filtered and concentrated under reduced pressure to give 8-(bromomethyl)-2-methylquinoline (1.50 g, 33.3%) as a solid.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 18 hours
  3. customThe solid was removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in DCM (100 mL)
  6. washwashed with saturated sodium bicarbonate and brine
  7. dry with materialdried (sodium sulfate)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-193f0f2594d6415da3e3d527d8e0f60b
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889704B2

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