Pyridine → HCID 53869643, Verbindung

HRID 342181Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 342181
Cl.[CH3:2][O:3][NH2:4].N1C=CC=CC=1.[CH3:11][NH:12][C:13](=[O:30])[C:14](=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH2:21][O:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][O:24]1>CO.[Cl-].[Na+].O>[CH3:2][O:3][N:4]=[C:14]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH2:21][O:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][O:24]1)[C:13]([NH:12][CH3:11])=[O:30]

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 18357814HCID 18357814, Verbindung

Produkt 1

HCID 53869643HCID 53869643, VerbindungAusbeute 60,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×HCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

Methoxyamine hydrochloride (0.33 g, 0.004 mol) was dissolved in methanol (4 ml), and pyridine (0.47 g, 0.006 mol) was added to the solution. To the mixture was added a mixed solution of N-methyl-2-oxo-2-[2-(2-tetrahydropyranyloxymethyl)phenyl]acetamide (0.55 g, 0.002 mol) and methanol (2 ml). The mixture was stirred under reflux for 2 hours. After completion of the reaction, half-saturated brine (100 ml) was added, and the mixture was extracted with dichloromethane (80 ml) twice. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane) to obtain an E/Z mixture of 2-methoxyimino-N-methyl-2-[2-(2-tetrahydropyranyloxymethyl)phenyl]acetamide (0.37 g, Yield: 60.4%) as a colorless oil.

Aufarbeitung

  1. temperatureunder reflux for 2 hours
  2. additionwas added
  3. extractionthe mixture was extracted with dichloromethane (80 ml) twice
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel chromatography (ethyl acetate/n-hexane)
  7. customto obtain

Quellen und Nachweise

ORD-Eintrag
ord-e6093a031e864708919aada10d14c2ab
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05856573

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