Methanol → methyl 3-nitro-1H-pyrazole-5-carboxylate

HRID 1188141Notes

Reaction equation

HRID 1188141 reaction equation
[N+:1]([C:4]1[NH:8][N:7]=[C:6]([C:9]([OH:11])=[O:10])[CH:5]=1)([O-:3])=[O:2].S(=O)(=O)(O)O.[CH3:17]O>>[N+:1]([C:4]1[NH:8][N:7]=[C:6]([C:9]([O:11][CH3:17])=[O:10])[CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 862226845-Nitro-1H-pyrazole-3-carboxylic acid

Product 1

HCID 135452337methyl 3-nitro-1H-pyrazole-5-carboxylateYield 86%

Procedure

5-Nitro-3-pyrazole-carboxylic acid (8 g, 50.90 mmol) and sulfuric acid (5 mL, 1.48 mmol) in methanol (200 mL) were heated to reflux for 4 hrs. The solvent was evaporated and the residue was resuspended in CH2Cl2 and washed with water and brine and dried Na2SO4. Methyl 5-nitro-1H-pyrazole-3-carboxylate (7.5 g, 86%) was obtained as a white solid.

Workup

  1. temperatureto reflux for 4 hrs
  2. customThe solvent was evaporated
  3. washwashed with water and brine and dried Na2SO4

Sources & evidence

ORD record
ord-08b16faa25fb453abdaa5934f8e9a4ed
Source dataset
uspto-grants-2014_03
Patent number
US08673940B2

Reaction notes

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