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

HRID 2307254Notes

Reaction equation

HRID 2307254 reaction equation
[N+:1]([O-:4])(O)=[O:2].[NH:5]1[C:9]([C:10]([OH:12])=[O:11])=[CH:8][C:7]([C:13]([OH:15])=[O:14])=[N:6]1.[OH-].[K+]>S(=O)(=O)(O)O>[N+:1]([C:8]1[C:7]([C:13]([OH:15])=[O:14])=[N:6][NH:5][C:9]=1[C:10]([OH:12])=[O:11])([O-:4])=[O:2]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 14797Potassium HydroxideHCID 76559Pyrazole-3,5-dicarboxylic acid

Product 1

HCID 14155004-nitro-1H-pyrazole-3,5-dicarboxylic acid

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
40 °C

Procedure

Fuming sulphuric acid (105 ml) was added dropwise over 45 minutes to ice-cooled fuming nitric acid (8 ml), so as to maintain the internal temperature below 20° C. Once addition was complete, the mixture was warmed to 40° C., pyrazole-3,5-dicarboxylic acid (1 25 g, 0.80 mol) was added portionwise over 75 minutes, so as to maintain the reaction temperature below 50° C., and the reaction then stirred at 60° C. for 18 hours. The cooled mixture was poured onto ice (1 Kg), and flaked potassium hydroxide carefully added with stirring, until the solution pH was 2. The resulting precipitate was filtered, and triturated with boiling water (500 ml), to afford the title compound as a white solid, 123 g.

Workup

  1. temperatureso as to maintain the internal temperature below 20° C
  2. additionOnce addition
  3. temperatureso as to maintain the reaction temperature below 50° C.
  4. customthe reaction
  5. additioncarefully added
  6. filtrationThe resulting precipitate was filtered
  7. customtriturated with boiling water (500 ml)

Sources & evidence

ORD record
ord-26168186efc44aab841846f9a12810e0
Source dataset
uspto-grants-2004_12
Patent number
US06831074B2

Reaction notes

Loading…