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

HRID 2058611

Reaction equation

HRID 2058611 reaction equation
[CH3:1][N:2]1[C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=[N:3]1.[N+:10]([O-])([OH:12])=[O:11].OS(O)(=O)=O.O=S(=O)=O>>[CH3:1][N:2]1[C:6]([C:7]([OH:9])=[O:8])=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=[N:3]1

Participants

4

Reactant 3

HCID 944Nitric AcidHCID 24681Fuming sulfuric acidHCID 6431581-methyl-1H-pyrazole-5-carboxylic acid

Product 1

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

Procedure

18.8 g of 1-methylpyrazole-5-carboxylic acid (mp 227° to 228° C.) are stirred in a mixture consisting of 23.5 of 100% strength nitric acid and 17 ml of 25% strength oleum for 8 hours at from 55° to 60° C. and for 4.5 hours at from 70° to 75° C. The mixture is poured onto ice and extracted with 9:1 methylene chloride/ethanol. The extract is concentrated. This yields 27 g of 1-methyl-4-nitropyrazole-5-carboxylic acid, mp 162° to 164° C., with decomposition (from ethyl acetate).

Workup

  1. additionThe mixture is poured onto ice
  2. extractionextracted with 9:1 methylene chloride/ethanol
  3. concentrationThe extract is concentrated

Sources & evidence

ORD record
ord-a58b9de55003430bbfed029fe6550e71
Source dataset
uspto-grants-1982_03
Patent number
US04317823

Linked notes

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