2-Methyl-2-(4-nitro-pyrazol-1-yl)-propan-1-ol → 2-(4-amino-1H-pyrazol-1-yl)-2-methylpropan-1-ol

HRID 714819Notes

Reaction equation

HRID 714819 reaction equation
[CH3:1][C:2]([N:6]1[CH:10]=[C:9]([N+:11]([O-])=O)[CH:8]=[N:7]1)([CH3:5])[CH2:3][OH:4]>C(O)C.[C].[Pd]>[NH2:11][C:9]1[CH:8]=[N:7][N:6]([C:2]([CH3:5])([CH3:1])[CH2:3][OH:4])[CH:10]=1

Participants

4

Reactant 1

HCID 1178409402-Methyl-2-(4-nitro-pyrazol-1-yl)-propan-1-ol

Product 1

HCID 901052112-(4-amino-1H-pyrazol-1-yl)-2-methylpropan-1-olYield 49.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of the crude 2-methyl-2-(4-nitro-1H-pyrazol-1-yl)propan-1-ol (36 g) obtained in Step G of Example 103 in ethanol (200 mL) was added 10% palladium-carbon (360 mg), and the mixture was stirred overnight at room temperature under hydrogen atmosphere (at normal pressure). The palladium-carbon was removed by filtration through Celite, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/methanol), and the obtained solid was washed with diisopropyl ether to give the title compound (15 g).

Workup

  1. customThe palladium-carbon was removed by filtration through Celite
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate/methanol)
  4. washthe obtained solid was washed with diisopropyl ether

Sources & evidence

ORD record
ord-f0cd1734c66e499e8cf662ebed5eaa12
Source dataset
uspto-grants-2015_11
Patent number
US09187453B2

Reaction notes

Loading…