Cyclopentylhydrazine hydrochloride → 1-cyclopentyl-3-ethyl-4-cyano-5-amino-1H-pyrazole

HRID 1736538Notes

Reaction equation

HRID 1736538 reaction equation
Cl.[CH:2]1([NH:7][NH2:8])[CH2:6][CH2:5][CH2:4][CH2:3]1.C[O-].[Na+].C(O[C:15](=[C:18]([C:21]#[N:22])[C:19]#[N:20])[CH2:16][CH3:17])C>C(O)C>[CH:2]1([N:7]2[C:21]([NH2:22])=[C:18]([C:19]#[N:20])[C:15]([CH2:16][CH3:17])=[N:8]2)[CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 212349Cyclopentylhydrazine hydrochlorideHCID 2314702-(1-Ethoxypropylidene)malononitrileHCID 10942334Sodium Methoxide

Product 1

HCID 158712691-cyclopentyl-3-ethyl-4-cyano-5-amino-1H-pyrazoleYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Cyclopentylhydrazine hydrochloride (20.9 g, 0.1 moles), 97% sodium methoxide (5.6 g, 0.1 moles) and ethanol (100 ml) were combined and stirred at room temperature under argon for 2.5 hours. (1-Ethoxypropylidene)malononitrile was added to the reaction mixture and the mixture was refluxed for 21 hours. The reaction mixture was cooled and the solvent was removed in vacuo. The residue was treated with water (150 ml) and the obtained precipitate was collected by filtration, washed with water and dried in a vacuum oven for 24 hours to afford 14.2 g (70%) of 1-cyclopentyl-3-ethyl-5-amino-1H-pyrazole-4-carbonitrile as a brown powder, m.p. 171°-173° C.

Workup

  1. temperaturethe mixture was refluxed for 21 hours
  2. temperatureThe reaction mixture was cooled
  3. customthe solvent was removed in vacuo
  4. additionThe residue was treated with water (150 ml)
  5. filtrationthe obtained precipitate was collected by filtration
  6. washwashed with water
  7. customdried in a vacuum oven for 24 hours

Sources & evidence

ORD record
ord-7d96401eb3e247d9ba211e684e72eeec
Source dataset
uspto-grants-1996_07
Patent number
US05541187

Reaction notes

Loading…