2-Hydrazinoethanol → 2-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)ethan-1-ol

HRID 2108355Notes

Reaction equation

HRID 2108355 reaction equation
[CH3:1][C:2]([CH3:9])([CH3:8])[C:3](=O)[CH2:4][C:5]#[N:6].[OH:10][CH2:11][CH2:12][NH:13][NH2:14]>CCO>[NH2:6][C:5]1[N:13]([CH2:12][CH2:11][OH:10])[N:14]=[C:3]([C:2]([CH3:9])([CH3:8])[CH3:1])[CH:4]=1

Participants

4

Reactant 2

HCID 80172-HydrazinoethanolHCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-

Product 1

HCID 162278772-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)ethan-1-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4,4-dimethyl-3-oxopentanenitrile (125 mg, 1.0 mmol) and 2-hydroxyethyl hydrazine (75 mg, 1.0 mmol) in EtOH was heated to 100° C. for 18 hours. The reaction mixture was concentrated under reduced pressure and the crude product was purified by flash chromatography (SiO2, 0% to 10% MeOH containing 1% NH4OH/CH2Cl2) to afford the desired amino-pyrazole.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe crude product was purified by flash chromatography (SiO2, 0% to 10% MeOH containing 1% NH4OH/CH2Cl2)

Sources & evidence

ORD record
ord-ab6ee110d6d944968134420222e52c82
Source dataset
uspto-grants-2009_04
Patent number
US07514435B2

Reaction notes

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