Ethanol → Ethyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate

HRID 1457925Notes

Reaction equation

HRID 1457925 reaction equation
C(OC=[C:5]([C:11]#[N:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.[CH3:13][NH:14][NH2:15].[CH2:16](O)C>>[NH2:12][C:11]1[N:15]([CH3:16])[N:14]=[CH:13][C:5]=1[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Participants

4

Reactant 3

HCID 702EthanolHCID 6061MethylhydrazineHCID 789432-Propenoic acid, 2-cyano-3-ethoxy-, ethyl ester

Product 1

HCID 271299Ethyl 5-amino-1-methyl-1H-pyrazole-4-carboxylateYield 84%

Procedure

To a solution of ethyl 3-ethoxy-2-cyanopropenoate (5.14 g) in ethanol (50 ml), was added methylhydrazine (1.61 ml), and the resulted mixture was refluxed for 12 h. The reaction mixture was evaporated under reduced pressure followed by silica-gel column chromatography (chloroform : methanol=50:1) to give 5-amino-4-ethoxycarbonyl-1-methylpyrazole (4.31 g, yield 84%).

Workup

  1. temperaturethe resulted mixture was refluxed for 12 h
  2. customThe reaction mixture was evaporated under reduced pressure

Sources & evidence

ORD record
ord-1522b988f02c4f64950aca5a358a48eb
Source dataset
uspto-grants-1998_12
Patent number
US05849779

Reaction notes

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