Potassium Nitrate → 5-nitro-1H-indazole-3-carboxylic Acid

HRID 1037999Notes

Reaction equation

HRID 1037999 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]([OH:12])=[O:11])=[N:2]1.[N+:13]([O-])([O-:15])=[O:14].[K+]>S(=O)(=O)(O)O>[N+:13]([C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[NH:1][N:2]=[C:3]2[C:10]([OH:12])=[O:11])([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 24434Potassium NitrateHCID 78250Indazole-3-carboxylic acid2×

Product 1

HCID 71446525-nitro-1H-indazole-3-carboxylic AcidYield 77.8%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a suspension of indazole-3-carboxylic acid (compound 53, 3.0 g, 18 mmol) in 18 mL of concentrated sulfuric acid at 0 C was added potassium nitrate (2.0 g, 18 mmol). The reaction was stirred overnight at room temperature, poured into 150 mL of ice and extracted three times with ethyl acetate. The combined organic layer was washed with brine, dried and concentrated to give compound 54 (2.9 g) as the major isomer.

Workup

  1. extractionextracted three times with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0a0fdad625654d2aac3086ba58f05015
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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