Hydrochloric Acid → 1-methyl-3-nitro-1H-pyrazole-4-carboxylic acid

HRID 1833582Notes

Reaction equation

HRID 1833582 reaction equation
[OH-:1].[Na+].[CH3:3][N:4]1[CH:8]=[C:7]([C:9]#N)[C:6]([N+:11]([O-:13])=[O:12])=[N:5]1.Cl.[OH2:15]>>[CH3:3][N:4]1[CH:8]=[C:7]([C:9]([OH:15])=[O:1])[C:6]([N+:11]([O-:13])=[O:12])=[N:5]1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 49131911-methyl-3-nitro-1H-pyrazole-4-carbonitrile

Product 1

HCID 183325151-methyl-3-nitro-1H-pyrazole-4-carboxylic acid

Procedure

A solution was made of 350 ml. of water, 35 gm. of NaOH, and 32 gm. of 1-methyl-3-nitro-4-pyrazolecarbonitrile. The solution was refluxed for 18 hours, cooled in an ice bath, and then acidified to pH 2 with concentrated HCl. A solid precipitated, which was filtered, washed with cold water, and recrystallized from methanol-water. The yield was 32.5 gm. of 1-methyl-3-nitro-4-pyrazolecarboxylic acid, m.p. 185°-187° C.

Workup

  1. temperatureThe solution was refluxed for 18 hours
  2. temperaturecooled in an ice bath
  3. customA solid precipitated
  4. filtrationwhich was filtered
  5. washwashed with cold water
  6. customrecrystallized from methanol-water

Sources & evidence

ORD record
ord-6608a8c5d3d748138d1b9e8f003932ee
Source dataset
uspto-grants-1978_01
Patent number
US04066776

Reaction notes

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