Sodium Iodide → 6-Bromo-1,2,3,4-tetrahydroquinoxalin-2-one

HRID 44187Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 44187
[NH2:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10](=[O:13])[CH2:11]Cl.[I-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C>[Br:8][C:6]1[CH:7]=[C:2]2[C:3](=[CH:4][CH:5]=1)[NH:9][C:10](=[O:13])[CH2:11][NH:1]2

Komponenten

5

Edukt 3

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 66911433N-(2-Amino-4-bromophenyl)-2-chloroacetamide

Produkt 1

HCID 669113076-Bromo-1,2,3,4-tetrahydroquinoxalin-2-oneAusbeute 34,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of N-(2-amino-4-bromophenyl)-2-chloroacetamide (4.5 g, 17.0 mmol), sodium iodide (101 mg, 2.0 mmol) and sodium carbonate (3.6 g, 33.8 mmol) in 300 ml acetonitrile was refluxed overnight under an atmosphere of nitrogen. Then the acetonitrile was removed under vacuum. The resulting solid was suspended in 150 ml water acidified to pH 5-6 with 1 N HCl. Extraction with ethyl acetate, washing of the combined organic layers with brine, drying over MgSO4, removing the solvent under reduced pressure and purification of the crude product by flash chromatography on silica gel (petroleum ether/ethyl acetate, 1.5/1) yielded 6-bromo-3,4-dihydroquinoxalin-2(1H)-one (1.3 g, 5.8 mmol, 34%) as yellow solid.

Aufarbeitung

  1. temperaturewas refluxed overnight under an atmosphere of nitrogen
  2. customThen the acetonitrile was removed under vacuum
  3. extractionExtraction with ethyl acetate
  4. washwashing of the combined organic layers with brine
  5. dry with materialdrying over MgSO4
  6. customremoving the solvent
  7. customunder reduced pressure and purification of the crude product by flash chromatography on silica gel (petroleum ether/ethyl acetate, 1.5/1)

Quellen und Nachweise

ORD-Eintrag
ord-42eee9138f1c4f8c95f371ff90bc6edb
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541404B2

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