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

HRID 350006

반응식

HRID 350006 반응식
[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

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 79772-ChloropyridineHCID 24758Sodium hydrideHCID 178469911HCID 178469911, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
180 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f51c58c1faa24ddf817c02bb5ae7e9b1
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07179823B1

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