2-(4-Nitro-1H-pyrazol-1-yl)ethan-1-ol → 2-(4-Amino-1H-pyrazol-1-yl)ethanol

HRID 624062Notes

Reaction equation

HRID 624062 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][N:7]([CH2:9][CH2:10][OH:11])[CH:8]=1)([O-])=O>CCOC(C)=O.CCO.O=[Pt]=O>[NH2:1][C:4]1[CH:5]=[N:6][N:7]([CH2:9][CH2:10][OH:11])[CH:8]=1

Participants

5

Reactant 1

HCID 1620552-(4-Nitro-1H-pyrazol-1-yl)ethan-1-ol

Product 1

HCID 284922672-(4-Amino-1H-pyrazol-1-yl)ethanol

Reagents, catalysts & solvents 3

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

Procedure

To a solution of 2-(4-nitro-1H-pyrazol-1-yl)ethanol (9.12 g, 58.07 mmol) in EtOAc (20 mL, degassed) and EtOH (60 mL, degassed), PtO2 (1.13 g, 5.81 mmol) was added and the reaction mixture was stirred at rt under a H2-atmosphere for 18 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-1H-pyrazol-1-yl)ethanol as a red oil, which was used in the next step without further purification. LC-MS conditions A: tR=0.14 min, [M+H]+=128.24.

Workup

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

Sources & evidence

ORD record
ord-5bcd7949ce0149e5889458edf52f2fa9
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

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