Methyl 1-methyl-5-nitro-1H-pyrazole-3-carboxylate → methyl 5-amino-1-methyl-1H-pyrazole-3-carboxylate

HRID 541428Notes

Reaction equation

HRID 541428 reaction equation
[CH3:1][N:2]1[C:6]([N+:7]([O-])=O)=[CH:5][C:4]([C:10]([O:12][CH3:13])=[O:11])=[N:3]1>CO.[Pd]>[NH2:7][C:6]1[N:2]([CH3:1])[N:3]=[C:4]([C:10]([O:12][CH3:13])=[O:11])[CH:5]=1

Participants

4

Reactant 1

HCID 50896836Methyl 1-methyl-5-nitro-1H-pyrazole-3-carboxylate

Product 1

HCID 13324840methyl 5-amino-1-methyl-1H-pyrazole-3-carboxylateYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of methyl 1-methyl-5-nitro-1H-pyrazole-3-carboxylate (351.2, 0.48 g, 2.60 mmol) in MeOH (15 ml) under nitrogen was added palladium on carbon (10%, 0.25 g). The flask was further degassed with nitrogen and filled with H2 through a balloon. The mixture was stirred at room temperature for 1.5 hours. After purging the system with nitrogen, the reaction mixture was filtered through a Celite cake and concentrated to give 363 mg (90%) of a white solid. m/z (ES+) 156 (M+H)+.

Workup

  1. customThe flask was further degassed with nitrogen
  2. additionfilled with H2 through a balloon
  3. customAfter purging the system with nitrogen
  4. filtrationthe reaction mixture was filtered through a Celite cake
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a816c534cab34aa99d425cc78aa7ee08
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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