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

HRID 1068388Notes

Reaction equation

HRID 1068388 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-d3ea3845f4d3466c861f9e089a0bd87d
Source dataset
uspto-grants-2001_06
Patent number
US06248894B1

Reaction notes

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