Dimethylformamide → ethyl 3-methyl-1-(2-pyridyl)-1H-pyrazole-4-carboxylate

HRID 1294190

反応式

HRID 1294190 の反応式
[CH3:1][C:2]1[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][NH:4][N:3]=1.Cl[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1.[H-].[Na+].CN(C)C=O>O>[CH3:1][C:2]1[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[N:3]=1

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 79772-ChloropyridineHCID 24758Sodium hydrideHCID 178469911HCID 178469911、化合物

生成物 1

HCID 9877977ethyl 3-methyl-1-(2-pyridyl)-1H-pyrazole-4-carboxylate収率 73%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
180 °C

実験手順

A mixture of ethyl 3-methyl-1H-pyrazole-4-carboxylate (7.95 g), 2-chloropyridine (5 ml), sodium hydride (0.60%, oil, 2.32 g) and N,N-dimethylformamide (150 ml) was stirred overnight at 180° C. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give ethyl 3-methyl-1-(2-pyridyl)-1H-pyrazole-4-carboxylate (8.31 g, yield 73%) as colorless crystals from a fraction eluted with ethyl acetate-hexane (1:9, volume ratio). The crystals were recrystallized from ethyl acetate-hexane. melting point: 79-80° C.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-aca10f5d6c0b467a886fb1b1abb105fa
出典データセット
uspto-grants-2007_07
特許番号
US07238716B2

関連ノート

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