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

HRID 1038002

Reaction equation

HRID 1038002 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 acid

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 (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 (90 mL total). The combined organic layer was washed with brine, dried and concentrated to give (54) (2.9 g) as the major product.

Workup

  1. extractionextracted three times with ethyl acetate (90 mL total)
  2. washThe combined organic layer was washed with brine
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-32e0917c4fb546c0a17cd670bb5ee70d
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Linked notes

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