2-(3,5-dimethyl-4-nitro-1H-pyrazol-1-yl)ethanol → HCID 28492268, compound

HRID 624067Notes

Reaction equation

HRID 624067 reaction equation
[CH3:1][C:2]1[C:6]([N+:7]([O-])=O)=[C:5]([CH3:10])[N:4]([CH2:11][CH2:12][OH:13])[N:3]=1>CCOC(C)=O.CCO.O=[Pt]=O>[NH2:7][C:6]1[C:2]([CH3:1])=[N:3][N:4]([CH2:11][CH2:12][OH:13])[C:5]=1[CH3:10]

Participants

5

Reactant 1

HCID 196169562-(3,5-dimethyl-4-nitro-1H-pyrazol-1-yl)ethanol

Product 1

HCID 28492268HCID 28492268, compound

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(3,5-dimethyl-4-nitro-1H-pyrazol-1-yl)ethanol (624 mg, 3.37 mmol) in EtOAc (1.2 mL, degassed) and EtOH (3.6 mL, degassed), PtO2 (66 mg, 0.34 mmol) was added and the reaction mixture was stirred at rt under a H2-atmosphere for 30 h. The mixture was diluted with EtOH, filtered over celite and the filter cake was rinsed with EtOH. The filtrate was concentrated to obtain 2-(4-amino-3,5-dimethyl-1H-pyrazol-1-yl)ethanol as a pale brown solid, which was used in the next step without further purification. LC-MS conditions A: tR=0.16 min, [M+H]+=156.29.

Workup

  1. filtrationfiltered over celite
  2. washthe filter cake was rinsed with EtOH
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-64b539c5722544fe886d95e3c08f3fba
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

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