Ethanol → HCID 178466834, compound

HRID 1880384Notes

Reaction equation

HRID 1880384 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:15]([O:17]CC)=[O:16])[CH:7]=[C:8]2[C:12]=1[NH:11][N:10]=[C:9]2[CH2:13][CH3:14])[CH3:2].[Li+].[OH-].C(O)C>C1COCC1>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:15]([OH:17])=[O:16])[CH:7]=[C:8]2[C:12]=1[NH:11][N:10]=[C:9]2[CH2:13][CH3:14])[CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 3939Lithium HydroxideHCID 178469308HCID 178469308, compound

Product 1

HCID 178466834HCID 178466834, compoundYield 100.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 7-ethoxy-3-ethyl-1H-indazole-5-carboxylate (389 mg, 1.48 mmol) in THF (13 mL) was added 1 M LiOH (3.0 mL, 3.0 mmol). The mixture was heated at reflux overnight. To the reaction was added trace amounts of ethanol to aid in solubilizing materials. Continue heating at reflux for an additional 2 hours. The reaction was cooled to room temperature, concentrated, triturated with 1 N HCl, the filtered solids were then washed with water and air dried to provide the title compound (347 mg, 97%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. temperatureContinue heating
  4. temperatureat reflux for an additional 2 hours
  5. concentrationconcentrated
  6. customtriturated with 1 N HCl
  7. washthe filtered solids were then washed with water and air
  8. customdried

Sources & evidence

ORD record
ord-ae2813dea05242e1b67f17572bde45b6
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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