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

HRID 270923Notes

Reaction equation

HRID 270923 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(Cl)(Cl)=O.[CH3:16]O>>[CH3:16][O:10][C:9]([C:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[NH:8][N:7]=1)=[O:11]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 862226845-Nitro-1H-pyrazole-3-carboxylic acid

Product 1

HCID 135452337methyl 3-nitro-1H-pyrazole-5-carboxylateYield 98%

Procedure

To a solution of 25.8 g (164 mmol) of 5-nitro-1H-pyrazole-3-carboxylic acid in 250 mL of anhydrous methanol (MeOH) was added dropwise 10.3 mL (141 mmol) of thionyl chloride, and the resulting mixture was heated at reflux overnight, then cooled to rt and concentrated to give 27.6 g (98% yield) of 5-nitro-1H-pyrazole-3-carboxylic acid methyl ester as a solid. 1H NMR (CDCl3) δ 6.08s, 1H), 3.91 (s, 3H).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux overnight
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-3dc63b68603444fca08fc0d8721f7c58
Source dataset
uspto-grants-2008_11
Patent number
US07449488B2

Reaction notes

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