Sulfuric Acid → HCID 178498471, compound

HRID 1754713Notes

Reaction equation

HRID 1754713 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:9]([OH:11])=[O:10])[NH:7][N:8]=1)([O-:3])=[O:2].S(=O)(=O)(O)O.[C:17](=O)([O-])[O-].[K+].[K+]>CO>[CH3:17][O:10][C:9]([C:6]1[NH:7][N:8]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)=[O:11]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 11430Potassium CarbonateHCID 178524578HCID 178524578, compound

Product 1

HCID 178498471HCID 178498471, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 5-nitro-2H-pyrazole-3-carboxylic acid (524, 10.0 g, 0.0637 mol) in methanol (100.0 mL) was added concentrated sulfuric acid (1.00 mL, 0.0180 mol). The reaction was stirred at room temperature overnight. The reaction was poured into aqueous potassium carbonate and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 20% ethyl acetate in hexane to give a white solid (525, 1.5 g, 13.8%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. custompurified by silica gel column chromatography
  6. washeluting with 20% ethyl acetate in hexane
  7. customto give a white solid (525, 1.5 g, 13.8%)

Sources & evidence

ORD record
ord-128d164f1a6e4bed86c90b05835c78c1
Source dataset
uspto-grants-2015_10
Patent number
US09169250B2

Reaction notes

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