N,1-dimethyl-4-nitropyrazole-3-carboxamide → 4-amino-N,1-dimethyl-1H-pyrazole-3-carboxamide

HRID 1045955Notes

Reaction equation

HRID 1045955 reaction equation
[CH3:1][NH: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]>[NH2:10][C:9]1[C:5]([C:3]([NH:2][CH3:1])=[O:4])=[N:6][N:7]([CH3:13])[CH:8]=1

Participants

4

Reactant 1

HCID 1256475N,1-dimethyl-4-nitropyrazole-3-carboxamide

Product 1

HCID 70175484-amino-N,1-dimethyl-1H-pyrazole-3-carboxamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

N,1-Dimethyl-4-nitropyrazole-3-carboxamide (1.23 g) was dissolved in MeOH (30 ml) and 10% Pd/C (0.3 g, 50% wet) was added. The mixture was stirred under a hydrogen atmosphere overnight and the catalyst filtered off. The solvent was removed in vacuo to yield 4-amino-N,1-dimethylpyrazole-3-carboxamide, 1.1 g. NMR Spectrum: (CDCl3) 2.93 (s, 3H), 3.76 (s, 3H), 4.41 (m, 2H), 6.62 (m, 1H), 6.89 (s, 1H); Mass spectrum: MH+ 155

Workup

  1. filtrationthe catalyst filtered off
  2. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-baec1464103341319127c106b80f0852
Source dataset
uspto-grants-2013_10
Patent number
US08569298B2

Reaction notes

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