Benzene → 2-Methoxy-5,6,7,8-tetrahydroquinoline

HRID 1359022Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1359022
[NH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]1=[O:11].[CH:12]1C=CC=CC=1.CI.CCCCCC.C(OCC)(=O)C>C1COCC1.C(=O)([O-])[O-].[Ag+2]>[CH3:12][O:11][C:2]1[CH:3]=[CH:4][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]=2[N:1]=1

Komponenten

7

Edukt 4

HCID 241BenzeneHCID 6328Methyl iodideHCID 2641061,2,5,6,7,8-Hexahydroquinolin-2-oneHCID 21226206Ethyl acetate hexane

Produkt 1

HCID 181802832-Methoxy-5,6,7,8-tetrahydroquinoline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418647HCID 178418647, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 5,6,7,8-tetrahydro-2-quinolone [Meyers, A. I. and Garcia-Munoz, G., J. Org. Chem. (1964) 29, 1435] (7.20 g, 48.32 mmol) and silver carbonate (9.33 g, 33.82 mmol) in THF (100 ml)-benzene (20 ml) was treated with methyl iodide (4.67 ml, 10.28 g, 72.48 mmol) and then heated at reflux for 18 h. On cooling to room temperature the mixture was filtered and the filtrate concentrated to give a brown oil which was subjected to column chromatography (silica, hexane-ethyl acetate, 2:1) to afford the title compound (4.40 g) as yellow oil MS (ES+) 164 (MH+). δH (CDCl3) 7,23 (1H, d, J 8.3 Hz), 6.47 (1H, d, J 8.3 Hz), 3.88 (3H, s), 2.78 (2H, t, J 5.9 Hz), 2.65 (2H, t, J 5.9 Hz) and 1.88-1.71 (4H, m).

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 18 h
  3. filtrationwas filtered
  4. concentrationthe filtrate concentrated
  5. customto give a brown oil which

Quellen und Nachweise

ORD-Eintrag
ord-d1e315409a22441fb682cf9e1feb2dd6
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06599908B1

Notizen zur Reaktion

Wird geladen…