3,3-Diethoxypropiononitrile → 1-cyclopropyl-1H-pyrazol-5-amine

HRID 1051683Notes

Reaction equation

HRID 1051683 reaction equation
C(O[CH:4](OCC)[CH2:5][C:6]#[N:7])C.Cl.Cl.[CH:13]1([NH:16][NH2:17])[CH2:15][CH2:14]1>C(O)C>[CH:13]1([N:16]2[C:6]([NH2:7])=[CH:5][CH:4]=[N:17]2)[CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 748513,3-DiethoxypropiononitrileHCID 717441821-Cyclopropylhydrazine dihydrochloride

Product 1

HCID 833829061-cyclopropyl-1H-pyrazol-5-amineYield 39.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A 100-mL round-bottom flask was charged with 3,3-diethoxypropanenitrile (0.600 g, 4.19 mmol), cyclopropylhydrazine di-hydrochloride (0.610 g, 4.21 mmol) and ethanol (20 mL), and the resulting solution stirred for 18 h at 80° C. The reaction mixture was cooled to room temperature and concentrated under vacuum. The residue was purified via column chromatography on silica gel (eluting with 10:1, dichloromethane/methanol) to afford 1-cyclopropyl-1H-pyrazol-5-amine (0.206 g, 36%) as light yellow oil. MS (ESI, pos. ion) m/z 124 [M+H]+.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated under vacuum
  3. customThe residue was purified via column chromatography on silica gel (eluting with 10:1, dichloromethane/methanol)

Sources & evidence

ORD record
ord-0bad107ea3dd4eb699fe8683abcddadf
Source dataset
uspto-grants-2016_07
Patent number
US09388161B2

Reaction notes

Loading…