Selenious Acid → (6-Chloro-3-formyl-quinoxalin-5-yl)-acetic acid methyl ester

HRID 505232

Reaktionsgleichung

[Se](O)(O)=[O:2].[CH3:5][O:6][C:7](=[O:21])[CH2:8][C:9]1[C:18]([Cl:19])=[CH:17][CH:16]=[C:15]2[C:10]=1[N:11]=[C:12]([CH3:20])[CH:13]=[N:14]2>O1CCOCC1.O>[CH3:5][O:6][C:7](=[O:21])[CH2:8][C:9]1[C:18]([Cl:19])=[CH:17][CH:16]=[C:15]2[C:10]=1[N:11]=[C:12]([CH:20]=[O:2])[CH:13]=[N:14]2

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

Selenious acid (645 mg, 5.00 mmol, 1.1 equiv) was added to a solution of (6-chloro-3-methyl-quinoxalin-5-yl)-acetic acid methyl ester in dioxane (30 ml). The reaction mixture was heated to 100° C. After 60 minutes, an additional portion of selenious acid (645 mg) was added, and heating was continued for another 60 minutes. After cooling, the reaction mixture was diluted with water, filtered, and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified via flash chromatography (gradient of hexane/EtOAc 100:0 to 80:20) to afford the title compound (966 mg, 81%). MS (ES+): 264 (M+H)+.

Aufarbeitung

temperatureheating
waitwas continued for another 60 minutes
temperatureAfter cooling
filtrationfiltered
extractionextracted with EtOAc
washThe combined organic layers were washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified via flash chromatography (gradient of hexane/EtOAc 100:0 to 80:20)

Quellen und Nachweise

ORD-Eintrag: ord-a31cc0070def436684d8bf55185ce669
Quelldatensatz: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07781438B2

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