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

HRID 1060176Notes

Reaction equation

HRID 1060176 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 75.4%

Procedure

A solution of ethyl (ethoxymethylene)cyanoacetate (68 g, 0.4 mol) and methylhydrazine (18.5 g, 0.4 mol) in 200 mL absolute ethanol was refluxed for 1.5 h, then cooled to RT and filtered. The filtrate was concentrated in vacuo and the residue was triturated with ether to give 54 g of crude ethyl 5-amino-1-methyl-1H-pyrazole-4-carboxylate in 75.4% yield.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe residue was triturated with ether

Sources & evidence

ORD record
ord-afd5614981014a32b14f56b6c4ed085e
Source dataset
uspto-grants-2003_02
Patent number
US06521603B2

Reaction notes

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