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

HRID 983918

Reaktionsgleichung

Reaktionsgleichung von HRID 983918
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[C:11]([O:16][CH2:17][CH2:18]Br)(=[O:15])[C:12]([CH3:14])=[O:13]>O1CCCC1>[CH2:17]([O:16][C:11](=[O:15])[C:12](=[O:13])[CH2:14][N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1)[CH3:18]

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

To a solution of 1,2,3,4-tetrahydroquinoline (75.5 mL, 0.59 mol) in tetrahydrofuran (300 mL) was added bromoethyl pyruvate (40 mL, 0.29 mol) dropwise over 30 minutes. Following 24 hours of stirring, the reaction mixture was filtered, the filter cake rinsed well with tetrahydrofuran (100 mL) and the filtrate concentrated under reduced pressure to dryness to give 79.7 g of the desired compound as a red oil.

Aufarbeitung

  1. filtrationthe reaction mixture was filtered
  2. washthe filter cake rinsed well with tetrahydrofuran (100 mL)
  3. concentrationthe filtrate concentrated under reduced pressure to dryness

Quellen und Nachweise

ORD-Eintrag
ord-6aed64f4d00e40d88332325f563924c9
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06867198B2

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