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

HRID 460675Notes

Reaction equation

HRID 460675 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 6.08 (s, 1H), 3.91 (s, 3H).

Workup

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

Sources & evidence

ORD record
ord-06122ad307134971bcfb2a08d66ccb50
Source dataset
uspto-grants-2007_03
Patent number
US07196111B2

Reaction notes

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