Nitric Acid → 1,3-dimethyl-4-nitro-1H-pyrazole-5-carboxylic acid

HRID 977932Notes

Reaction equation

HRID 977932 reaction equation
S(=O)(=O)(O)O.[N+:6]([O-:9])(O)=[O:7].[CH3:10][N:11]1[C:15]([C:16]([OH:18])=[O:17])=[CH:14][C:13]([CH3:19])=[N:12]1>>[CH3:10][N:11]1[C:15]([C:16]([OH:18])=[O:17])=[C:14]([N+:6]([O-:9])=[O:7])[C:13]([CH3:19])=[N:12]1

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 5877211,3-Dimethyl-1H-pyrazole-5-carboxylic acid

Product 1

HCID 12297711,3-dimethyl-4-nitro-1H-pyrazole-5-carboxylic acid

Procedure

One-hundred and twelve grams concentrated sulfuric acid is added to 42 ml 90% nitric acid at 70°-80° C. To this 39 grams 1,3-dimethylpyrazole-5-carboxylic acid is added in portions over one hour such that temperature does not go over 90° C. After 2.5 hours the reaction mixture was cooled and poured over ice. The resulting percipitate was filtered, dried, and recrystallized in ethanol, to produce 1,3-dimethyl-4-nitropyrazol-5-carboxylic acid having mp 141°-142° C.

Workup

  1. customdoes not go over 90° C
  2. temperatureAfter 2.5 hours the reaction mixture was cooled
  3. additionpoured over ice
  4. filtrationThe resulting percipitate was filtered
  5. customdried
  6. customrecrystallized in ethanol

Sources & evidence

ORD record
ord-d76741352bd347c997bdc64742ec6e4f
Source dataset
uspto-grants-1987_05
Patent number
US04663326

Reaction notes

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