Hydrazine hydrate (1:1) → 4-(Pyridin-2-yl)-1H-pyrazole-3,5-diamine

HRID 490109

Reaction equation

HRID 490109 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]([C:10]#[N:11])[C:8]#[N:9].O.[NH2:13][NH2:14]>CCO>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[C:10]([NH2:11])=[N:13][NH:14][C:8]=1[NH2:9]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 102409162-Pyridylmalononitrile

Product 1

HCID 576745884-(Pyridin-2-yl)-1H-pyrazole-3,5-diamineYield 52.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-pyridin-2-yl-malononitrile (0.65 g, 4.59 mmol) and hydrazine hydrate (225 μL, 4.59 mmol) in EtOH (5 mL) was heated to reflux and stirred for 16 hours. The reaction mixture was cooled down to room temperature and filtered. The resulting solid was washed with Et2O to provide the title compound as a light tan solid (0.42 g, 52%). The filtrate was evaporated to dryness and purified by silica gel chromatography eluting with NH4OH:MeOH:CH2Cl2 (0.5:5:95) to give a further 63.3 mg (8%) of the desired product. MS (ES+) 176, (ES−) 174. δH (DMSO-d6) 5.45 (4H, br s), 6.98 (1H, t), 7.57 (1H, d), 7.69 (1H, t), 8.46 (1H, d), 10.55 (1H, br s).

Workup

  1. temperaturewas heated
  2. temperatureto reflux
  3. filtrationfiltered
  4. washThe resulting solid was washed with Et2O

Sources & evidence

ORD record
ord-aef4521d22c647d0bbaad0dfb900de50
Source dataset
uspto-grants-2009_05
Patent number
US07528138B2

Linked notes

Loading…