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

HRID 1294190

반응식

HRID 1294190 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 (7.95 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.

후처리

  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

출처 및 근거

ORD 기록
ord-aca10f5d6c0b467a886fb1b1abb105fa
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07238716B2

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