Butanedione → 5-Bromo-8-(3,5-dimethoxy-phenyl)-2,3-dimethyl-quinoxaline

HRID 1189844

Reaktionsgleichung

Reaktionsgleichung von HRID 1189844
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[C:10]([O:16][CH3:17])[CH:9]=2)=[C:4]([NH2:18])[C:3]=1[NH2:19].[CH3:20][C:21](=O)[C:22](=O)[CH3:23]>CCO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([O:16][CH3:17])[CH:11]=[C:12]([O:14][CH3:15])[CH:13]=2)=[C:4]2[C:3]=1[N:19]=[C:21]([CH3:20])[C:22]([CH3:23])=[N:18]2

Komponenten

4

Edukt 2

HCID 650Butanedione2×HCID 592928784-Bromo-3',5'-dimethoxy-biphenyl-2,3-diamine

Produkt 1

HCID 669145915-Bromo-8-(3,5-dimethoxy-phenyl)-2,3-dimethyl-quinoxalineAusbeute 83,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 4-bromo-3′,5′-dimethoxy-biphenyl-2,3-diamine (Step 85.7) (3 g, 9.3 mmol) and 2,3-butanedione (1 mL, 11.1 mmol, 1.2 equiv) in EtOH (60 mL) was stirred at reflux for 2 h, allowed to cool to rt and stirred for 16 h. Additional 2,3-butanedione (0.4 ml) was added. The reaction mixture was stirred at reflux for 2 h, allowed to cool and concentrated to half of the initial volume. The resulting yellow precipitate was collected vacuum filtration providing 2.9 g of the title compound: ES-MS: 373.1/375.0 [M+H]+; tR=5.60 min (System 1).

Aufarbeitung

  1. temperatureat reflux for 2 h
  2. stirringstirred for 16 h
  3. stirringThe reaction mixture was stirred
  4. temperatureat reflux for 2 h
  5. temperatureto cool
  6. concentrationconcentrated to half of the initial volume
  7. customThe resulting yellow precipitate was collected
  8. filtrationvacuum filtration

Quellen und Nachweise

ORD-Eintrag
ord-b0e26bf7396249f0969d69234978c7d5
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08674099B2

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