Water → 5-Chloro-3,4-dihydroquinoxalin-2(1H)-one

HRID 558964Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 558964
C([N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][C:13]=2[Cl:15])[NH:8][C:7](=[O:16])[CH2:6]1)(C)(C)C.[BH4-].[Na+].O>S(=O)(=O)(O)O>[Cl:15][C:13]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:14]=1[NH:5][CH2:6][C:7](=[O:16])[NH:8]2

Komponenten

5

Edukt 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 107763594-tert-Butyl-5-chloro-3,4-dihydro-1H-quinoxalin-2-one

Produkt 1

HCID 105593595-Chloro-3,4-dihydroquinoxalin-2(1H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

4-tert-Butyl-5-chloro-3,4-dihydro-1H-quinoxalin-2-one from Example 12C (1.5 g, 6.1 mmol) was suspended in 2N sulphuric acid (45 ml) and stirred for 18 h. The mixture was filtered and the filtrate was neutralised with sodium hydrogen carbonate, extracted with EtOAc, dried and evaporated. The residue was taken up in ethanol (30 ml) and cooled in an ice/water bath. Sodium borohydride (460 mg, 12 mmol) was added and the mixture was allowed to warm to room temperature over 2 h. Water (1 ml) was added and the mixture was evaporated. The residue was triturated with ice-cold water, filtered, washed with ice-cold water and dried in vacuo over phosphorous pentoxide to give an orange solid; yield 550 mg, 49%.

Aufarbeitung

  1. filtrationThe mixture was filtered
  2. extractionextracted with EtOAc
  3. customdried
  4. customevaporated
  5. temperaturecooled in an ice/water bath
  6. customthe mixture was evaporated
  7. customThe residue was triturated with ice-cold water
  8. filtrationfiltered
  9. washwashed with ice-cold water
  10. dry with materialdried in vacuo over phosphorous pentoxide
  11. customto give an orange solid

Quellen und Nachweise

ORD-Eintrag
ord-54f57c16c2534a318d0c0f1572f3d10a
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063038B2

Notizen zur Reaktion

Wird geladen…