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

HRID 1294190Notes

Reaction equation

HRID 1294190 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
180 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-aca10f5d6c0b467a886fb1b1abb105fa
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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