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

HRID 43105

反応式

HRID 43105 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 592929205,8-Dibromo-2-methyl-quinoxaline収率 33.6%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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).

後処理

  1. temperatureat reflux
  2. temperatureto cool
  3. filtrationfiltered

出典と根拠

ORDレコード
ord-68953635f53a4eeea8b15bac2fe1149e
出典データセット
uspto-grants-2013_09
特許番号
US08536175B2

関連ノート

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