Water → 1,2,3,4-Tetrahydro-1-methylquinoline

HRID 279985

Reaktionsgleichung

Reaktionsgleichung von HRID 279985
[NH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.O.[C:12](=O)(O)[O-].[Na+].COS(OC)(=O)=O>C(OCC)(=O)C>[CH3:12][N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 694601,2,3,4-TetrahydroquinolineHCID 516892Sodium Bicarbonate

Produkt 1

HCID 681091,2,3,4-Tetrahydro-1-methylquinolineAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

1,2,3,4-Tetrahydroquinoline (6.66 g, 50 mmol) was added to 40 ml of water, 40 ml of ethyl acetate, and 5.04 g (60 mmol) of sodium bicarbonate to which was added 5.68 ml (60 mmol) of dimethylsulfate dropwise. The reaction was stirred at room temperature for 21/2 hours, and the organic layer was separated. The aqueous layer was extracted with ethyl acetate, then the organic layers were combined and evaporated to give 4.56 g (62% yield) of the title compound. NMR (CDCl3) δ 1.93 (quintet, 2, CH2), 2.74 (tr, 2, CH2), 2.81 (s, 3, NMe), 3.17 (tr, 2, CH2), 6.55 (m, 2, Ar), 6.97 (m, 2, Ar).

Aufarbeitung

  1. customthe organic layer was separated
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-0bf6822aa32f48ef9a629c7030fa7b45
Quelldatensatz
uspto-grants-1986_05
Patentnummer
US04587341

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