Phosphorus oxychloride → 2-Chloro-6-methoxyquinoxaline

HRID 250036

Reaktionsgleichung

Reaktionsgleichung von HRID 250036
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=O)[CH:7]=[N:6]2.COC1C=C2C(N=CC(=O)N2)=CC=1.P(Cl)(Cl)([Cl:29])=O>>[Cl:29][C:8]1[CH:7]=[N:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=1

Komponenten

4

Edukt 3

HCID 24813Phosphorus oxychlorideHCID 4913197-Methoxy-1,2-dihydroquinoxalin-2-oneHCID 134377076-Methoxyquinoxalin-2(1H)-one

Produkt 1

HCID 126864122-Chloro-6-methoxyquinoxalineAusbeute 35 %

Versuchsvorschrift

A mixture of 6-methoxyquinoxalin-2(1H)-one and 7-methoxyquinoxalin-2(1H)-one (5.67 g, 32.20 mmol) was refluxed in phosphorus oxychloride (120 mL) for 1 h. The reaction was concentrated and quenched by addition of ice, then basified with sodium carbonate, and extracted with ethyl acetate (3×200 mL). The organic layers were combined and concentrated in vacuo. The crude product was absorbed onto sodium sulfate and purified by column chromatography (0 to 5% ethyl acetate/hexanes) to afford 2-chloro-6-methoxyquinoxaline (2.21 g, 11.36 mmol, 35% yield). 1H NMR (400 MHz, CDCl3) δ ppm 8.69 (s, 1 H), 7.88 (d, J=9.32 Hz, 1 H), 7.43 (dd, J=9.32, 2.77 Hz, 1 H), 7.37 (d, J=2.77 Hz, 1 H), 3.95 (s, 3 H).

Aufarbeitung

  1. concentrationThe reaction was concentrated
  2. customquenched by addition of ice
  3. extractionextracted with ethyl acetate (3×200 mL)
  4. concentrationconcentrated in vacuo
  5. customThe crude product was absorbed onto sodium sulfate
  6. custompurified by column chromatography (0 to 5% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-25e0870ba1884210bdecf6b3e8813416
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863291B2

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