Acetic Anhydride → N-[1-(4-bromopyridin-2-yl)-4-methoxybutyl]acetamide

HRID 656233Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 656233
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH:8]([NH2:14])[CH2:9][CH2:10][CH2:11][O:12][CH3:13])[CH:3]=1.[C:15](OC(=O)C)(=[O:17])[CH3:16].[OH-].[Na+]>C(O)(=O)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH:8]([NH:14][C:15](=[O:17])[CH3:16])[CH2:9][CH2:10][CH2:11][O:12][CH3:13])[CH:3]=1

Komponenten

6

Edukt 3

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 686532511-(4-Bromopyridin-2-yl)-4-methoxybutylamine

Produkt 1

HCID 68652850N-[1-(4-bromopyridin-2-yl)-4-methoxybutyl]acetamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A solution of 32.0 g of 1-(4-bromopyridin-2-yl)-4-methoxybutylamine in 150 ml of glacial acetic acid is mixed with 37 ml of acetic anhydride. The reaction solution is stirred at 50° C. for 30 minutes and then diluted with ethyl acetate. It is basified with 2M sodium hydroxide solution, and the phases are separated. The aqueous phase is extracted with ethyl acetate (2×). The combined organic phases are evaporated. The title compound is obtained as a yellowish solid from the residue by flash chromatography (SiO2 60 F). Rf=0.38 (EtOAc-methanol 9:1); Rt=2.33 (Gradient I).

Aufarbeitung

  1. customthe phases are separated
  2. extractionThe aqueous phase is extracted with ethyl acetate (2×)
  3. customThe combined organic phases are evaporated

Quellen und Nachweise

ORD-Eintrag
ord-216e598d7e3e4400a697266c81525bd9
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071651B2

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