Hydrochloric Acid → methyl 1H-indazole-3-carboxylate

HRID 1162595Notes

Reaction equation

HRID 1162595 reaction equation
[CH3:1]O.[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]([OH:14])=[O:13])=[N:4]1.Cl>O1CCOCC1>[CH3:1][O:13][C:12]([C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[NH:3][N:4]=1)=[O:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 78250Indazole-3-carboxylic acid

Product 1

HCID 657476methyl 1H-indazole-3-carboxylate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To the methanol solution of 1H-indazole-3-carboxylic acid (162 mg, 1 mmol) was added 4N HCl in dioxane (2 mL) and the mixture was stirred at the room temperature for 24 h. After evaporation of the volatiles, the mixture was partitioned between aqueous NaHCO3 solution and ethyl acetate. The aqueous phase was extracted with ethyl acetate (2×15 mL), and the combined organic layer was dried over sodium sulfate. The volatiles were removed, and the residue was filtered over silica gel to provide 1H-Indazole-3-carboxylic acid methyl ester (123 mg). LCMS m/z: 177 (M+1)+.

Workup

  1. customAfter evaporation of the volatiles
  2. customthe mixture was partitioned between aqueous NaHCO3 solution and ethyl acetate
  3. extractionThe aqueous phase was extracted with ethyl acetate (2×15 mL)
  4. dry with materialthe combined organic layer was dried over sodium sulfate
  5. customThe volatiles were removed
  6. filtrationthe residue was filtered over silica gel

Sources & evidence

ORD record
ord-4426e564cf1f41008f04d47441141217
Source dataset
uspto-grants-2010_10
Patent number
US07820704B2

Reaction notes

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