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

HRID 611001Notes

Reaction equation

HRID 611001 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-2af8627f3f14470ebf9d37548925b1ba
Source dataset
uspto-grants-1999_12
Patent number
US05998466

Reaction notes

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