Hydrazine hydrate (1:1) → trans 5-(-2-methylcyclopropyl)-1H-pyrazol-3-amine

HRID 1484959Notes

Reaction equation

HRID 1484959 reaction equation
[CH3:1][CH:2]1[CH2:4][CH:3]1[C:5](=O)[CH2:6][C:7]#[N:8].O.[NH2:11][NH2:12]>C(O)C>[CH3:1][C@@H:2]1[CH2:4][C@H:3]1[C:5]1[NH:12][N:11]=[C:7]([NH2:8])[CH:6]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 431156733-(2-Methylcyclopropyl)-3-oxopropanenitrile

Product 1

HCID 51675220trans 5-(-2-methylcyclopropyl)-1H-pyrazol-3-amineYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The crude 3-(2-methylcyclopropyl)-3-oxopropanenitrile was dissolved in ethanol (50 mL) and hydrazine hydrate (0.83 mL, 17 mmol) was added. The solution was maintained at reflux for 10 hours and then the solvent evaporated under vacuum. The residue was redissolved in methylene chloride and washed several times with brine. The organic layer was dried over anhydrous sodium sulfate and the solvent evaporated to give compound trans 5-(−2-methylcyclopropyl)-1H-pyrazol-3-amine (1 g, 79%, three step).

Workup

  1. temperatureThe solution was maintained
  2. temperatureat reflux for 10 hours
  3. customthe solvent evaporated under vacuum
  4. dissolutionThe residue was redissolved in methylene chloride
  5. washwashed several times with brine
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-f054e4e6d4c74c10b448aec12f03042d
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

Loading…