2-Hydrazinoethanol → 2-[5-amino-3-(pyridin-2-yl)-1H-pyrazol-1-yl]ethan-1-ol

HRID 1260314Notes

Reaction equation

HRID 1260314 reaction equation
O=[C:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)[CH2:3][C:4]#[N:5].[OH:12][CH2:13][CH2:14][NH:15][NH2:16]>CCO>[NH2:5][C:4]1[N:15]([CH2:14][CH2:13][OH:12])[N:16]=[C:2]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=2)[CH:3]=1

Participants

4

Reactant 2

HCID 80172-HydrazinoethanolHCID 115718233-Oxo-3-(pyridin-2-yl)propanenitrile

Product 1

HCID 628254882-[5-amino-3-(pyridin-2-yl)-1H-pyrazol-1-yl]ethan-1-olYield 80.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-oxo-3-pyridin-2-yl-propionitrile (0.5 g, 3.4 mmol; CAS 54123-21-6) in EtOH (20 ml) was treated with 2-hydroxyethylhydrazine (0.7 ml, 10.3 mmol). The reaction mixture was refluxed overnight, then concentrated. After silica gel chromatography using a CH2Cl2/MeOH gradient, the product was obtained as viscous yellow oil (0.56 g, 80%).

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-99d03ce82d7e425883dd325908a8281c
Source dataset
uspto-grants-2013_06
Patent number
US08470820B2

Reaction notes

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