Water → 5,6,7,8-Tetrahydro-7-(methylamino)quinoline

HRID 1461292Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1461292
[Cl-].[CH3:2][NH3+:3].[N:4]1[C:13]2[CH:12]=[CH:11][CH2:10][CH2:9][C:8]=2[CH:7]=[CH:6][CH:5]=1.O.[OH-].[Na+]>CO.[Cl-].[Na+].O.C(OCC)(=O)C.C(OCC)(=O)C.C1(C)C=CC=CC=1>[CH3:2][NH:3][CH:11]1[CH2:12][C:13]2[N:4]=[CH:5][CH:6]=[CH:7][C:8]=2[CH2:9][CH2:10]1

Komponenten

9

Edukt 4

HCID 962WaterHCID 11637Methanamine, hydrochloride (1:1)HCID 14798Sodium HydroxideHCID 123183175,6-Dihydroquinoline

Produkt 1

HCID 148359215,6,7,8-Tetrahydro-7-(methylamino)quinolineAusbeute 83,2 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 887MethanolLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittelHCID 21584019Toluene ethylacetateLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

A solution of methylammonium chloride (1.35 g, 20 mmol) in methanol (2 ml) was added to 5,6-dihydroquinoline (1.31 g, 10 mmol) in methanol (2 ml) and the solution was heated under reflux for 21h, poured onto a mixture of water (25 ml) and brine (25 ml), and basified with 10N-NaOH (25 ml). The mixture was extracted with chloroform (3×25 ml), and the extracts were dried (Na2SO4) and concentrated in vacuo to give an orange oil. Chromatography [alumina; ethyl acetate-toluene (1:4)→ethyl acetate] gave the product (1.35 g) as an oil which was identical to the compound isolated in Example 2.

Aufarbeitung

  1. temperaturethe solution was heated
  2. extractionThe mixture was extracted with chloroform (3×25 ml)
  3. dry with materialthe extracts were dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customto give an orange oil

Quellen und Nachweise

ORD-Eintrag
ord-8fed0ceb97524b93b7d35b54634c528a
Quelldatensatz
uspto-grants-1991_12
Patentnummer
US05075303

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