Methylhydrazine → 5-amino-1,3-dimethyl-1H-pyrazole-4-carbonitrile

HRID 876901Notes

Reaction equation

HRID 876901 reaction equation
C(O[C:4](=[C:6]([C:9]#[N:10])[C:7]#[N:8])[CH3:5])C.[CH3:11][NH:12][NH2:13]>C(O)C>[NH2:8][C:7]1[N:12]([CH3:11])[N:13]=[C:4]([CH3:5])[C:6]=1[C:9]#[N:10]

Participants

4

Reactant 2

HCID 6061MethylhydrazineHCID 79450(1-Ethoxyethylidene)malononitrile

Product 1

HCID 2198705-amino-1,3-dimethyl-1H-pyrazole-4-carbonitrileYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(1-Ethoxy-ethylidene)-malononitrile 1a (10 g, 73.45 mmol) was added portionwise to a mixture of N-methylhydrazine (1 equiv., 3.88 ml) in ethanol (50 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-1,3-dimethyl-1H-pyrazole-4-carbonitrile 2a as white crystalline solid (9.85 g, 68%).

Workup

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

Sources & evidence

ORD record
ord-5532ff4f93b94d5babb9eaddcfdd84b4
Source dataset
uspto-grants-2015_03
Patent number
US08987280B2

Reaction notes

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