Triethylamine → 5-AMINO-1-ETHYL-1H-PYRAZOLE-4-CARBONITRILE

HRID 876902Notes

Reaction equation

HRID 876902 reaction equation
C(OC=C(C#N)[C:6]#[N:7])C.[C:10](O)(=O)[C:11](O)=O.[CH2:16]([NH:18][NH2:19])[CH3:17].[CH2:20]([N:22](CC)CC)C>C(O)C>[NH2:22][C:20]1[N:19]([CH2:10][CH3:11])[N:18]=[CH:16][C:17]=1[C:6]#[N:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 671522-(Ethoxymethylene)propanedinitrileHCID 96181Hydrazine, ethyl-, ethanedioate (1:1)

Product 1

HCID 107967925-AMINO-1-ETHYL-1H-PYRAZOLE-4-CARBONITRILEYield 53%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethoxy-methylidenemalononitrile 1b (1.73 g, 14.17 mmol) was added portionwise to a mixture of N-ethylhydrazine oxalate (1 equiv., 2.13 ml) and triethylamine (2.1 equiv., 4.17 ml) in ethanol (20 ml) and the reaction mixture was refluxed for 1 hour, cooled to room temperature, precipitate filtered, washed with ethanol and dried to give 5-amino-1-ethyl-1H-pyrazole-4-carbonitrile 2b as white crystalline solid (1.02 g, 53%).

Workup

  1. temperaturethe reaction mixture was refluxed for 1 hour
  2. filtrationprecipitate filtered
  3. washwashed with ethanol
  4. customdried

Sources & evidence

ORD record
ord-a7f218b8b3bb407c9c97a29f81b01d08
Source dataset
uspto-grants-2015_03
Patent number
US08987280B2

Reaction notes

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