Water → diethyl N-(4-ethylcyclohexen-1-yl)-aminomethylenemalonate

HRID 649591

Reaktionsgleichung

Reaktionsgleichung von HRID 649591
[CH2:1]([CH:3]1[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1)[CH3:2].[NH2:10][CH:11]=[C:12]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[CH2:1]([CH:3]1[CH2:8][CH2:7][C:6]([NH:10][CH:11]=[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:5][CH2:4]1)[CH3:2]

Komponenten

6

Edukt 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 795064-EthylcyclohexanoneHCID 226751Diethyl (aminomethylidene)propanedioate

Produkt 1

HCID 14153004diethyl N-(4-ethylcyclohexen-1-yl)-aminomethylenemalonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 12.6 g of 4-ethylcyclohexanone, 17.0 g of diethyl aminomethylenemalonate, and 950 mg of p-toluenesulfonic acid in 170 ml of toluene is heated at reflux for 48 hours with a water separator, under nitrogen atmosphere. The solvent is removed under nitrogen atmosphere and under vacuum, and the residue purified by flash column chromatooraphy on a silica qel column eluted with methylene chloride. The desired product, diethyl N-(4-ethylcyclohexen-1-yl)-aminomethylenemalonate is obtained as an oil. The purified product in 90 ml Dowtherm is aded to 300 ml Dowtherm preheated to 250° under nitrogen atmosphere. After heating at 240°-245° for 4 hours the reaction mixture is cooled and allowed to stand at room temperature overnight. The precipitate which formed is filtered off, washed with hexane and air-dried. Recrystallization form isopropanol after treatment with decolorizing carbon affords ethyl 4-hydroxy-6-ethyl-5,6,7,8-tetrahydroquinoline-3-carboxylate m.p. 218°-220°.

Aufarbeitung

  1. temperatureis heated
  2. customThe solvent is removed under nitrogen atmosphere and under vacuum
  3. customthe residue purified by flash column chromatooraphy on a silica qel column
  4. washeluted with methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-d10468cb8acb40e2bd82b66e43989ade
Quelldatensatz
uspto-grants-1988_04
Patentnummer
US04740512

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