methyl 3-nitro-1H-pyrazole-5-carboxylate → HCID 178498460, compound

HRID 1488167Notes

Reaction equation

HRID 1488167 reaction equation
[N+:1]([C:4]1[NH:8][N:7]=[C:6]([C:9]([O:11][CH3:12])=[O:10])[CH:5]=1)([O-])=O>CO>[NH2:1][C:4]1[NH:8][N:7]=[C:6]([C:9]([O:11][CH3:12])=[O:10])[CH:5]=1

Participants

3

Reactant 1

HCID 135452337methyl 3-nitro-1H-pyrazole-5-carboxylate2×

Product 1

HCID 178498460HCID 178498460, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into a 100-mL round-bottom flask, was placed a solution of methyl 5-nitro-1H-pyrazole-3-carboxylate (compound 260.1, 2.5 g, 14.6 mmol) in methanol (10 mL). The system was purged with nitrogen, then palladium/carbon (10 wt % Pd, 0.8 g) was added. The system was charged with hydrogen (1 atm) and the mixture was stirred overnight at room temperature. The system was purged with nitrogen, then the solids were removed by filtration. The filtrate was concentrated under reduced pressure to obtain the title compound as an off-white solid (1.5 g, 73%).

Workup

  1. customInto a 100-mL round-bottom flask, was placed
  2. customThe system was purged with nitrogen
  3. additionpalladium/carbon (10 wt % Pd, 0.8 g) was added
  4. additionThe system was charged with hydrogen (1 atm)
  5. customThe system was purged with nitrogen
  6. customthe solids were removed by filtration
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-443011be60e84a5cbfc064ae215e2fd2
Source dataset
uspto-grants-2016_08
Patent number
US09428502B2

Reaction notes

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