Ethanolamine → HCID 66914997, Verbindung

HRID 880406

Reaktionsgleichung

Reaktionsgleichung von HRID 880406
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.[CH2:10]([CH2:12][NH2:13])[OH:11].[OH-].[Na+]>O.O1CCOCC1>[CH3:8][C:6]1[CH:5]=[C:4]([CH3:9])[N:3]=[C:2]([O:11][CH2:10][CH2:12][NH2:13])[CH:7]=1

Komponenten

6

Edukt 3

HCID 700EthanolamineHCID 14798Sodium HydroxideHCID 125083782-Chloro-4,6-dimethylpyridine

Produkt 1

HCID 66914997HCID 66914997, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

From 2-chloro-4,6-dimethylpyridine by treatment with ethanolamine and sodium hydroxide in a mixture of water and dioxane to afford 2-(4,6-dimethyl-pyridin-2-yloxy)-ethylamine, followed by heating with 1-fluoro-4-nitrobenzene in ethanol to give [2-(4,6-dimethyl-pyridin-2-yloxy)-ethyl]-(4-nitro-phenyl)-amine. The free amine is protected as a trifluoroacetamide by treatment with trifluoroacetic anhydride and sodium hydride in THF then the nitro group is reduced with zinc powder in the presence of ammonium chloride in ethanol. Following coupling with the appropriately-selected acid chloride, a final treatment with lithium hydroxide in methanol removes the trifluoroacetamide to give the final compound described.

Quellen und Nachweise

ORD-Eintrag
ord-670e8ae524cb41b8b6ebd2e9f88f5142
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08993574B2

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