1-Hexylpyrrole-2,5-dione → 5-Hexyl-3-isopropyl-3(3-nitrophenyl)-3a,6a-dihydropyrrolo(3,4-c)pyrazole-4,6(3H,5H) dione

HRID 1826448ノート

反応式

HRID 1826448 の反応式
[CH3:1][CH:2]([CH3:15])[C:3]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[CH:7]=1)=[N:4][NH2:5].[CH2:16]([N:22]1[C:26](=[O:27])[CH:25]=[CH:24][C:23]1=[O:28])[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>O1CCOCC1.[O-2].[O-2].[Mn+4]>[CH2:16]([N:22]1[C:23](=[O:28])[CH:24]2[CH:25]([N:5]=[N:4][C:3]2([CH:2]([CH3:15])[CH3:1])[C:6]2[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[CH:7]=2)[C:26]1=[O:27])[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

参加物

5

反応物 2

HCID 4641341-Hexylpyrrole-2,5-dioneHCID 598980482-Methyl-1-(3-nitrophenyl)-1-propanone hydrazone

生成物 1

HCID 221412935-Hexyl-3-isopropyl-3(3-nitrophenyl)-3a,6a-dihydropyrrolo(3,4-c)pyrazole-4,6(3H,5H) dione

試薬・触媒・溶媒 2

HCID 178418406HCID 178418406、化合物触媒HCID 312751,4-Dioxane溶媒2 回

実験手順

2-Methyl-1-(3-nitrophenyl)-1-propanone hydrazone (Preparation 57, 0.52 g, 2.5 mmol) was dissolved in dioxan (10 ml) and manganese dioxide (grade CMD-1 from Sumitomo, 5.2 g, 60.0 mmol) was added portionwise and the reaction mixture was stirred at room temperature for 20 minutes. This solution was filtered over a pad of Celite® dropwise, directly into a solution of 1-hexyl-1H-pyrrole-2,5-dione (Preparation 56, 0.54 g, 3.0 mmol) in dioxan (10 ml). The Celite® pad was washed with dioxan (40 ml) to ensure complete addition of the reactants and then the reaction mixture was stoppered and stirred for 72 h. The reaction mixture was purified by chromatography using a Biotage Flash 40S™ cartridge packed with silica gel (40 g), eluting with petroleum ether:ethyl acetate (4:1). The title compound was obtained as a yellow solid (0.65 g, 67%).

後処理

  1. filtrationThis solution was filtered over a pad of Celite® dropwise
  2. washThe Celite® pad was washed with dioxan (40 ml)
  3. additionaddition of the reactants
  4. stirringstirred for 72 h
  5. customThe reaction mixture was purified by chromatography
  6. washeluting with petroleum ether:ethyl acetate (4:1)

出典と根拠

ORDレコード
ord-651e66e528904af6b704d87deeec935c
出典データセット
uspto-grants-2006_05
特許番号
US07049444B2

反応ノート

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