7-Methoxyquinoline → 7-Methoxy-1,2,3,4-tetrahydroquinoline

HRID 1520178Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1520178
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1>CO.O=[Pt]=O>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][CH2:9][NH:10]2)=[CH:5][CH:4]=1

Komponenten

4

Edukt 1

HCID 786667-Methoxyquinoline

Produkt 1

HCID 162443887-Methoxy-1,2,3,4-tetrahydroquinolineAusbeute 73,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 345198Adams' catalystKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 7-methoxyquinoline (2.0 g, 12.56 mmol) in methanol (60 ml) was added PtO2 (180 mg, 0.79 mmol). H2 (g) was introduced into above solution and the reaction was stirred overnight at room temperature and then the solids were filtered off. The organics were concentrated in vacuo to give a residue, which was purified by silica gel column chromatography with 3% ethyl acetate in petroleum ether to afford 7-methoxy-1,2,3,4-tetrahydroquinoline as a light yellow oil (1.5 g, 73%).

Aufarbeitung

  1. additionH2 (g) was introduced into above solution
  2. filtrationthe solids were filtered off
  3. concentrationThe organics were concentrated in vacuo
  4. customto give a residue, which
  5. customwas purified by silica gel column chromatography with 3% ethyl acetate in petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-762f89ecda7745aba699fc390fd16151
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073902B2

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