1-(4-Nitrobenzoyl)-1,2,3,4-tetrahydroquinoline → (4-aminophenyl)(3,4-dihydroquinolin-1(2H)-yl)methanone

HRID 745045

Reaktionsgleichung

Reaktionsgleichung von HRID 745045
[N+:1]([C:4]1[CH:21]=[CH:20][C:7]([C:8]([N:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][CH2:12][CH2:11]2)=[O:9])=[CH:6][CH:5]=1)([O-])=O.[H][H]>C(O)C.[Pd]>[NH2:1][C:4]1[CH:21]=[CH:20][C:7]([C:8]([N:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][CH2:12][CH2:11]2)=[O:9])=[CH:6][CH:5]=1

Komponenten

5

Edukt 2

HCID 37636931-(4-Nitrobenzoyl)-1,2,3,4-tetrahydroquinolineHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 2984117(4-aminophenyl)(3,4-dihydroquinolin-1(2H)-yl)methanoneAusbeute 97,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 10% Pd-C (5 g) in ethanol (500 ml) is added 1-(4-nitrobenzoyl)-1,2,3,4-tetrahydroquinoline (53.4 g) and the mixture is subjected to catalytic reduction at ordinary temperature under atmospheric pressure of hydrogen. After the reduction, 10% Pd-C is removed by filtration, and the filtrate is concentrated under reduced pressure to give 1-(4-aminobenzoyl)-1,2,3,4-tetrahydroquinoline (46.7 g) as yellow powder, m.p. 185°-188° C.

Aufarbeitung

  1. customAfter the reduction, 10% Pd-C is removed by filtration
  2. concentrationthe filtrate is concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e8aac1cea9164d018bc289c932d92af7
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05559230

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