N,N,1,3-tetramethyl-4-nitropyrazole-5-carboxamide → 4-amino-N,N,1,3-tetramethylpyrazole-5-carboxamide

HRID 2058607Notes

Reaction equation

HRID 2058607 reaction equation
[CH3:1][N:2]([CH3:15])[C:3]([C:5]1[N:9]([CH3:10])[N:8]=[C:7]([CH3:11])[C:6]=1[N+:12]([O-])=O)=[O:4].[H][H]>CO.[Pd]>[NH2:12][C:6]1[C:7]([CH3:11])=[N:8][N:9]([CH3:10])[C:5]=1[C:3]([N:2]([CH3:1])[CH3:15])=[O:4]

Participants

5

Reactant 2

HCID 20549790N,N,1,3-tetramethyl-4-nitropyrazole-5-carboxamideHCID 178418361HCID 178418361, compound

Product 1

HCID 205499434-amino-N,N,1,3-tetramethylpyrazole-5-carboxamideYield 98.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

19.0 g of N,N,1,3-tetramethyl-4-nitropyrazole-5-carboxamide in 400 ml of methanol are hydrogenated in the presence of 2.0 g of 10% strength palladium-on-charcoal in an autoclave at a hydrogen pressure of from 80 to 110 bars (8,000 to 11,000 kPa) for 8 hours at room temperature. The mixture is filtered, and the solvent is removed by distillation in vacuo to yield 16.1 g of crystalline 4-amino-N,N,1,3-tetramethylpyrazole-5-carboxamide, mp 116° to 118° C. (from ethyl acetate).

Workup

  1. filtrationThe mixture is filtered
  2. customthe solvent is removed by distillation in vacuo

Sources & evidence

ORD record
ord-341b93ae12bc4dbe8f6037cec108abee
Source dataset
uspto-grants-1982_03
Patent number
US04317823

Reaction notes

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