1,2,3,4-Tetrahydroquinoline → ethyl 3-(3,4-dihydroquinolin-1(2H)-yl)-2-oxopropanoate

HRID 910060

Reaktionsgleichung

Reaktionsgleichung von HRID 910060
[C:1]([O:6][CH2:7][CH2:8]Br)(=[O:5])[C:2]([CH3:4])=[O:3].[NH:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12][CH2:11]1>O1CCCC1>[CH2:7]([O:6][C:1](=[O:5])[C:2](=[O:3])[CH2:4][N:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12][CH2:11]1)[CH3:8]

Komponenten

4

Edukt 2

HCID 694601,2,3,4-TetrahydroquinolineHCID 86587973Bromoethyl pyruvate

Produkt 1

HCID 20729419ethyl 3-(3,4-dihydroquinolin-1(2H)-yl)-2-oxopropanoateAusbeute 111,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Add bromoethyl pyruvate (40 mL, 0.29 mol) to a solution of 1,2,3,4-tetrahydroquinoline (75.5 mL, 0.59 mol) in tetrahydrofuran (300 mL) dropwise over 30 minutes. Stir for 24 hours, filter the reaction mixture, rinse the filter cake well with tetrahydrofuran (100 mL), and concentrate the filtrate under reduced pressure to provide the desired compound as a red oil (79.7 g).

Aufarbeitung

  1. filtrationfilter the reaction mixture
  2. washrinse the filter cake well with tetrahydrofuran (100 mL)
  3. concentrationconcentrate the filtrate under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-bb50bfcab1d44a3ea0fedbc98d023025
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08022065B2

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