7-Methylquinoline → 7-Methyl-1,2,3,4-tetrahydroquinoline

HRID 1515332

Reaktionsgleichung

Reaktionsgleichung von HRID 1515332
[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1>CO.[Pd]>[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][NH:9]2)=[CH:4][CH:3]=1

Komponenten

4

Edukt 1

HCID 119277-Methylquinoline

Produkt 1

HCID 4586807-Methyl-1,2,3,4-tetrahydroquinolineAusbeute 99,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 7-methylquinoline (2.00 g) in methanol (40 ml), 10% palladium on activated carbon (200 mg) was added and stirred overnight under a hydrogen atmosphere (60 psi) at room temperature. After the reaction mixture was filtered through celite, the solvent was distilled off under reduced pressure and the resulting residue was purified by silica gel column chromatography (eluting solvent: n-hexane:ethyl acetate=20:1 to 10:1) to give the titled compound, i.e., 7-methyl-1,2,3,4-tetrahydroquinoline (2.05 g) as a yellow oil.

Aufarbeitung

  1. filtrationAfter the reaction mixture was filtered through celite
  2. distillationthe solvent was distilled off under reduced pressure
  3. customthe resulting residue was purified by silica gel column chromatography (eluting solvent: n-hexane:ethyl acetate=20:1 to 10:1)

Quellen und Nachweise

ORD-Eintrag
ord-47db28d475234f448b93f82a61268022
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08222417B2

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