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

HRID 2307813Notes

Reaction equation

HRID 2307813 reaction equation
[C:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][N:5]=1)([OH:3])=[O:2].Cl.[CH3:14]O>>[CH3:14][O:2][C:1]([C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][N:5]=1)=[O:3]

Participants

4

Reactant 3

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

Product 1

HCID 657476methyl 1H-indazole-3-carboxylate

Procedure

A solution of 3-carboxyindazole (2.0 g; 12.3 mmol) and conc.HCl (2 mL) in MeOH (50 mL) was heated at reflux overnight, concentrated, diluted with 2N NaOH (aq), and extracted with EtOAc. The extracts were rinsed with brine, dried (MgSO4), and concentrated to provide the desired product.

Workup

  1. temperatureat reflux overnight
  2. concentrationconcentrated
  3. additiondiluted with 2N NaOH (aq)
  4. extractionextracted with EtOAc
  5. washThe extracts were rinsed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-31d8f367d1474c649b8a89c6657acb97
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Reaction notes

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