N,N,1-trimethyl-4-nitropyrazole-3-carboxamide → 4-Amino-N,N,1-trimethyl-1H-pyrazole-3-carboxamide

HRID 1045957Notes

Reaction equation

HRID 1045957 reaction equation
[CH3:1][N:2]([CH3:14])[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]([N:2]([CH3:14])[CH3:1])=[O:4])=[N:6][N:7]([CH3:13])[CH:8]=1

Participants

4

Reactant 1

HCID 67076071N,N,1-trimethyl-4-nitropyrazole-3-carboxamide

Product 1

HCID 653550564-Amino-N,N,1-trimethyl-1H-pyrazole-3-carboxamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

N,N,1-Trimethyl-4-nitropyrazole-3-carboxamide (1.22 g) was dissolved in MeOH (35 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,N,1-trimethylpyrazole-3-carboxamide, 810 mg. NMR Spectrum: (CDCl3) 3.06 (m, 3H), 3.44 (m, 3H), 3.78 (s, 3H), 4.51 (m, 2H), 6.90 (s, 1H); Mass spectrum: MH+ 169

Workup

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

Sources & evidence

ORD record
ord-3877ac76c5854fd19a2bf794ec5b1ec7
Source dataset
uspto-grants-2013_10
Patent number
US08569298B2

Reaction notes

Loading…