Hexanal → 3-Butylimidazo[1,2-a]pyridine-6-carboxylic acid

HRID 14236

Reaktionsgleichung

[CH:1](=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[NH2:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][N:10]=1>C(O)(C)C.O>[CH2:3]([C:2]1[N:10]2[CH:11]=[C:12]([C:13]([OH:15])=[O:14])[CH:16]=[CH:17][C:9]2=[N:8][CH:1]=1)[CH2:4][CH2:5][CH3:6]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

To hexanal (1.02 g, 10.2 mmol) in 15 mL of isopropyl alcohol-water (4:1 v/v) was added CuCl2 (1.37 g, 10.2 mmol). The mixture was heated at 80° C. for 2.5 h, then cooled. The solids were removed by filtration and the filtrate was added to 6-aminonicotinic acid (1.35 g, 10 mmol). The mixture was stirred overnight at room temperature, then heated at reflux 32 h. After cooling, the solvents were removed under reduced pressure and MeOH was added to the residue. The resulting solid was removed by filtration and the filtrate was concentrated to dryness. MeOH was again added, and the resulting solid removed by filtration. After concentration of the filtrate, the residue was chromatographed on silica gel using MeOH-dichloromethane (33/67) to give 0.26 g of 3-butylimidazo[1,2-a]pyridine-6-carboxylic acid.

Aufarbeitung

temperaturecooled
customThe solids were removed by filtration
temperatureheated
temperatureat reflux 32 h
temperatureAfter cooling
customthe solvents were removed under reduced pressure and MeOH
additionwas added to the residue
customThe resulting solid was removed by filtration
concentrationthe filtrate was concentrated to dryness
additionMeOH was again added
customthe resulting solid removed by filtration
customAfter concentration of the filtrate, the residue was chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag: ord-67a4f68931c34afa8b6e232c4a21c8db
Quelldatensatz: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07727997B2

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