Methanol → HCID 178498471, compound

HRID 449678Notes

Reaction equation

HRID 449678 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[NH:7][N:8]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)=[O:11]

Participants

4

Reactant 3

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

Product 1

HCID 178498471HCID 178498471, compoundYield 90%

Procedure

To a solution of 5-nitro-1H-pyrazole-3-carboxylic acid (2.0 g, 12.7 mmol) in anhydrous methanol (20 ml) at to 0° C. was added thionyl chloride (3.94 g, 2.42 ml, 33.1 mmol) drop wise. The resulting solution was heated to reflux for 2 h. The cooled solution was evaporated to dryness and the residue was treated with methanol (20 ml). The resulting solution was evaporated to dryness to give 5-nitro-2H-pyrazole-3-carboxylic acid methyl ester (1.97 g, 90%) as a white solid.

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux for 2 h
  3. customThe cooled solution was evaporated to dryness
  4. additionthe residue was treated with methanol (20 ml)
  5. customThe resulting solution was evaporated to dryness

Sources & evidence

ORD record
ord-6db7bf2bb4a04158b1cba9eedb5daed8
Source dataset
uspto-grants-2013_07
Patent number
US08481540B2

Reaction notes

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