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

HRID 2271049Notes

Reaction equation

HRID 2271049 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 acidYield 76%

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 finning nitric acid (88 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 (125 g, 0.80 mol) 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 (123 g, 76%) as a white solid. m.p. 325-327° C.

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-1e74307799eb4e7cae79b1af603cc90e
Source dataset
uspto-grants-2001_12
Patent number
US06333330B1

Reaction notes

Loading…