Ethanol → HCID 178492734, compound

HRID 1880351Notes

Reaction equation

HRID 1880351 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]([O:15]CC)=[O:14])[CH:6]=[C:7]2[C:11]=1[NH:10][N:9]=[C:8]2[CH3:12].[Li+].[OH-].C(O)C>C1COCC1>[CH3:12][C:8]1[C:7]2[C:11](=[C:3]([O:2][CH3:1])[CH:4]=[C:5]([C:13]([OH:15])=[O:14])[CH:6]=2)[NH:10][N:9]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 3939Lithium HydroxideHCID 178469302HCID 178469302, compound

Product 1

HCID 178492734HCID 178492734, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 7-methoxy-3-methyl-1H-indazole-5-carboxylate (516 mg, 2.08 mmol) in THF (17 mL) was added 1 M LiOH (4.2 mL, 4.2 mmol) and the mixture was heated at reflux overnight. Analysis indicated the presence of small amounts of unreacted starting material; therefore, a small amount of ethanol was added to assist in solubilizing materials. Heating was continued for an additional 2 hours before concentrating to dryness. The residue was triturated with 1 N HCl, the solids were isolated by filtration, washed with water and air dried overnight to provide the title compound as an off-white solid (417 mg, 91%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux overnight
  3. temperatureHeating
  4. concentrationbefore concentrating to dryness
  5. customThe residue was triturated with 1 N HCl
  6. customthe solids were isolated by filtration
  7. washwashed with water and air
  8. customdried overnight

Sources & evidence

ORD record
ord-136cbc6ae4a44b7caaa8ca4d20993e69
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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