Methyl 1-methyl-4-nitro-1H-pyrazole-3-carboxylate → methyl 4-amino-1-methyl-1H-pyrazole-3-carboxylate

HRID 2368246Notes

Reaction equation

HRID 2368246 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:9]([N+:10]([O-])=O)=[CH:8][N:7]([CH3:13])[N:6]=1)=[O:4]>CO.[Pd]>[CH3:1][O:2][C:3]([C:5]1[C:9]([NH2:10])=[CH:8][N:7]([CH3:13])[N:6]=1)=[O:4]

Participants

4

Reactant 1

HCID 54775322Methyl 1-methyl-4-nitro-1H-pyrazole-3-carboxylate

Product 1

HCID 7017722methyl 4-amino-1-methyl-1H-pyrazole-3-carboxylateYield 84.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 1-methyl-4-nitro-1H-pyrazole-3-carboxylic acid methyl ester (4.8 g, 25.94 mmol) in dry MeOH (100 ml) was thoroughly purged with argon, treated with 10% Pd—C (2.7 g, 2.59 mmol), and again purged with argon. Then the reaction mixture was hydrogenated under a balloon pressure of hydrogen at rt for overnight. The reaction mixture was filtered through a bed of celite. The filtrate was concentrated and dried to give the title compound as gray-white solid (3.4 g, 84%), which was used in the next reaction step without further purification.

Workup

  1. customagain purged with argon
  2. filtrationThe reaction mixture was filtered through a bed of celite
  3. concentrationThe filtrate was concentrated
  4. customdried

Sources & evidence

ORD record
ord-3e33690299a747fabc0afb02e78e31e2
Source dataset
uspto-grants-2014_04
Patent number
US08703768B2

Reaction notes

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