N-Methoxy-N-methyl-3-nitro-1H-pyrazole-5-carboxamide → HCID 178502676, compound

HRID 336840Notes

Reaction equation

HRID 336840 reaction equation
[CH3:1][O:2][N:3]([CH3:14])[C:4]([C:6]1[CH:10]=[C:9]([N+:11]([O-])=O)[NH:8][N:7]=1)=[O:5]>O1CCCC1.CO>[NH2:11][C:9]1[NH:8][N:7]=[C:6]([C:4]([N:3]([O:2][CH3:1])[CH3:14])=[O:5])[CH:10]=1

Participants

3

Reactant 1

HCID 136352997N-Methoxy-N-methyl-3-nitro-1H-pyrazole-5-carboxamide

Product 1

HCID 178502676HCID 178502676, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

6.40 g (32.00 mmol) of N-methoxy-N-methyl-5-nitro-1H-pyrazole-3-carboxamide are dissolved in 500 ml of tetrahydrofuran/methanol mixture (50:50). The solution is purged under argon and 220 mg of palladium on charcoal (10%) are added. The solution is then degassed with hydrogen and stirred under a hydrogen atmosphere for 18 h. After degassing with argon, the solution is filtered on Celite and the solvent is concentrated to yield 5.2 g of 5-amino-N-methoxy-N-methyl-1H-pyrazole-3-carboxamide in the form of a white solid.

Workup

  1. customThe solution is purged under argon
  2. addition220 mg of palladium on charcoal (10%) are added
  3. customThe solution is then degassed with hydrogen
  4. customAfter degassing with argon
  5. filtrationthe solution is filtered on Celite
  6. concentrationthe solvent is concentrated

Sources & evidence

ORD record
ord-5ac8a05483d84dea954a3115b2911eac
Source dataset
uspto-grants-2014_11
Patent number
US08889711B2

Reaction notes

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