Nitric Acid → 1-Methyl-4-nitro-1H-pyrazole-5-carboxylic acid

HRID 1702436Notes

Reaction equation

HRID 1702436 reaction equation
[CH3:1][N:2]1[C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=[N:3]1.S(=O)(=O)(O)O.[N+:15]([O-])([OH:17])=[O:16]>>[CH3:1][N:2]1[C:6]([C:7]([OH:9])=[O:8])=[C:5]([N+:15]([O-:17])=[O:16])[CH:4]=[N:3]1

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 6431581-methyl-1H-pyrazole-5-carboxylic acid

Product 1

HCID 5926231-Methyl-4-nitro-1H-pyrazole-5-carboxylic acid

Procedure

A quantity comprising 69.0 gm (0.547 mol) of 1-methyl-1H-pyrazole-5-carboxylic acid of m.p.: 227°-228° C. (R. Huttel and M. E. Schon, Liebigs Ann. Chem 625, 55 [1959]) was added in small portions to a mixture of 200 ml of concentrated sulfuric acid and 60 ml of 90% fuming nitric acid under stirring. The temperature of the mixture rose from 75° C. at the beginning to a maximum temperature of 95° C. After the exothermal reaction was finished, heating was continued for 30 minutes up to 95° C. The cold mixture was stirred into 300 gm of cracked ice, and the resulting ice-cold suspension was filtered off by suction filtration. The filtration residue was washed with water, and after recrystallization from ethyl acetate, 44.0 gm (47% of theory) of pale yellow crystals were obtained.

Workup

  1. customrose from 75° C. at the beginning to a maximum temperature of 95° C
  2. customAfter the exothermal reaction
  3. temperatureheating
  4. filtrationthe resulting ice-cold suspension was filtered off by suction filtration
  5. washThe filtration residue was washed with water
  6. customafter recrystallization from ethyl acetate, 44.0 gm (47% of theory) of pale yellow crystals
  7. customwere obtained

Sources & evidence

ORD record
ord-58e74a8a159543719ee4a6e06b53c6e4
Source dataset
uspto-grants-1983_04
Patent number
US04381303

Reaction notes

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