Methylglyoxal → 5,8-Dibromo-2-methyl-quinoxaline

HRID 43105

Reaktionsgleichung

Reaktionsgleichung von HRID 43105
[CH3:1][C:2]([CH:4]=O)=O.[Br:6][C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[C:9]([NH2:14])[C:8]=1[NH2:15]>CCO>[Br:6][C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[C:9]2[C:8]=1[N:15]=[CH:1][C:2]([CH3:4])=[N:14]2

Komponenten

4

Edukt 2

HCID 880MethylglyoxalHCID 118215323,6-Dibromobenzene-1,2-diamine

Produkt 1

HCID 592929205,8-Dibromo-2-methyl-quinoxalineAusbeute 33,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A 40% aqueous solution of methylglyoxal (6.7 M, 6.3 mL, 112 mmol, 1.48 equiv) was added to a suspension of 3,6-dibromo-benzene-1,2-diamine (Step 1.6) (20 g, 75.5 mmol) in EtOH (400 mL). The reaction mixture was stirred for 2 h at it and for 0.5 h at reflux, allowed to cool and filtered to afford 7.66 g of the title compound. The filtrate was concentrated and the residue triturated in EtOAc and filtered. The filtrate was concentrated and the residue was purified by silica gel column chromatography (Hex/EtOAc, 1:0→9:1) to provide additional 2.15 g of the title compound. The title compound: ESI-MS: 300.9/302.9/304.9 [M+H]+; tR=4.81 min (System 1); TLC: Rf=0.90 (Hex/EtOAc, 1:1).

Aufarbeitung

  1. temperatureat reflux
  2. temperatureto cool
  3. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-68953635f53a4eeea8b15bac2fe1149e
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536175B2

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