Methylamine Acetate → 4-(5-Chloroindol-3-yl)-2-methylamino-4-oxo-2-butenoic acid ethyl ester

HRID 1634303Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1634303
[CH2:1]([O:3][C:4](=[O:20])[C:5](O)=[CH:6][C:7]([C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([Cl:18])[CH:16]=2)[NH:11][CH:10]=1)=[O:8])[CH3:2].C(O)(=O)C.[CH3:25][NH2:26]>CCO>[CH2:1]([O:3][C:4](=[O:20])[C:5]([NH:26][CH3:25])=[CH:6][C:7]([C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([Cl:18])[CH:16]=2)[NH:11][CH:10]=1)=[O:8])[CH3:2]

Komponenten

4

Edukt 2

HCID 13000541Methylamine AcetateHCID 178473094HCID 178473094, Verbindung

Produkt 1

HCID 600774434-(5-Chloroindol-3-yl)-2-methylamino-4-oxo-2-butenoic acid ethyl esterAusbeute 38 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 0.59 g (2.0 mmol) of 4-(5-chloroindol-3-yl)-2-hydroxy-4-oxo-2-butenoic acid ethyl ester prepared in Example 1(1) in 95% EtOH (10 ml) was added 0.55 g (6.0 mmol) of methylamine acetate. After refluxing for 2.5 hours, the reaction mixture was concentrated and the residue was dissolved in ethyl acetate. The ethyl acetate was washed with water, dried, and then concentrated. The resulting residue was chromatographed on silica gel (ethyl acetate as eluant) to give 0.23 g of the titled compound as oil. Yield: 38%.

Aufarbeitung

  1. temperatureAfter refluxing for 2.5 hours
  2. concentrationthe reaction mixture was concentrated
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe ethyl acetate was washed with water
  5. customdried
  6. concentrationconcentrated
  7. customThe resulting residue was chromatographed on silica gel (ethyl acetate as eluant)

Quellen und Nachweise

ORD-Eintrag
ord-d09f4fa0dddd421480a90db56d397824
Quelldatensatz
uspto-grants-2003_01
Patentnummer
US06506787B2

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