Phenylhydrazine → Ethyl 3-methyl-1-phenylpyrazole-5-carboxylate

HRID 1816620ノート

反応式

HRID 1816620 の反応式
O=[C:2]([CH2:8][C:9](=O)[CH3:10])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:12]1([NH:18][NH2:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C(O)(=O)C>[CH3:10][C:9]1[CH:8]=[C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[N:18]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:19]=1.[CH3:10][C:9]1[N:18]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:19]=[C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH:8]=1

参加物

5

反応物 2

HCID 7516PhenylhydrazineHCID 69208Ethyl 2,4-dioxovalerate

生成物 2

HCID 2746772Ethyl 3-methyl-1-phenylpyrazole-5-carboxylateHCID 10900438Ethyl 5-methyl-1-phenyl-1H-pyrazole-3-carboxylate

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
100 °C

実験手順

2 ml ethyl 2,4-dioxovalerate and 1.2 g phenyl hydrazine were dissolved in 20 ml acetic acid, followed by stirring at 100° C. for 2 hours. After evaporating acetic acid, ethyl acetate was added to the residue. The mixture was washed with aqueous sodium hydrogencarbonate solution and brine, dried over anhydrous magnesium sulfate and evaporated. The residue was subjected to silica gel column chromatography, to give 0.37 g of ethyl 3-methyl-1-phenyl-1H-5-pyrazolecarboxylate with hexane:ethyl acetate (14:1) and 0.46 g of ethyl 5-methyl-1-phenyl-1H-3-pyrazolecarboxylate with hexane:ethyl acetate (9:1).

後処理

  1. customAfter evaporating acetic acid, ethyl acetate
  2. additionwas added to the residue
  3. washThe mixture was washed with aqueous sodium hydrogencarbonate solution and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated

出典と根拠

ORDレコード
ord-f288b1ed3a0a4d9b8821f343cbfd88bf
出典データセット
uspto-grants-2005_04
特許番号
US06884821B1

反応ノート

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