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

HRID 2074143Notes

Reaction equation

HRID 2074143 reaction equation
S(Cl)(Cl)=O.[N+:5]([C:8]1[NH:12][N:11]=[C:10]([C:13]([OH:15])=[O:14])[CH:9]=1)([O-:7])=[O:6].[CH3:16]O>>[CH3:16][O:14][C:13]([C:10]1[CH:9]=[C:8]([N+:5]([O-:7])=[O:6])[NH:12][N:11]=1)=[O:15]

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 88%

Procedure

Thionyl chloride (1 mL) was added to a solution of 5-nitro-3-pyrazolecarboxylic acid (9.800 g, 62.3 mmol) in anhydrous methanol (100 mL), the reaction mixture was heated to reflux overnight. The solvents was removed in vacuo, the residue was recrystallized from ethyl acetate and hexanes to give 5-nitro-1H-pyrazole-3-carboxylic acid methyl ester (9.42 g, 88%). 1H NMR (300 MHz, CDCl3) δ 7.38 (s, 1H), 3.99 (s, 3H). MS (ES+) m/z 170.0 (M+1).

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux overnight
  3. customThe solvents was removed in vacuo
  4. customthe residue was recrystallized from ethyl acetate and hexanes

Sources & evidence

ORD record
ord-68506e41c79e40b9b81712f7d3127018
Source dataset
uspto-grants-2011_04
Patent number
US07919496B2

Reaction notes

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