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

HRID 350006

反応式

HRID 350006 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 (7.59 g), 2-chloropyridine (5 ml), sodium hydride (60%, oily, 2.32 g) and N,N-dimethylformamide (150 ml) was stirred at 180° C. overnight. The reaction mixture was poured into water, which was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography to obtain ethyl 3-methyl-1-(2-pyridyl)-1H-pyrazole-4-carboxylate (8.31 g, yield 73%) from the fraction eluted with ethyl acetate-hexane (1:9, volume ratio). This was recrystallized from ethyl acetate-hexane. Melting point: 79–80° C.

後処理

  1. extractionwas extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-f51c58c1faa24ddf817c02bb5ae7e9b1
出典データセット
uspto-grants-2007_02
特許番号
US07179823B1

関連ノート

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