Sodium Hydroxide → HCID 22260948, compound

HRID 1610074Notes

Reaction equation

HRID 1610074 reaction equation
[O:1]1[C:5]([C:6]2[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([C:15]([O:17]C)=[O:16])[CH:13]=3)[NH:8][N:7]=2)=[CH:4][C:3]2[CH:19]=[CH:20][CH:21]=[CH:22][C:2]1=2.[OH-].[Na+]>CO.O1CCCC1>[O:1]1[C:5]([C:6]2[C:14]3[C:9](=[CH:10][CH:11]=[C:12]([C:15]([OH:17])=[O:16])[CH:13]=3)[NH:8][N:7]=2)=[CH:4][C:3]2[CH:19]=[CH:20][CH:21]=[CH:22][C:2]1=2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22260735HCID 22260735, compound

Product 1

HCID 22260948HCID 22260948, compoundYield 122.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 275 mg of methyl 3-benzo[b]furan-2-yl-1H-5-indazolecarboxylate in 3 ml methanol and 3 ml tetrahydrofuran was added 1.5 ml of 5 N aqueous sodium hydroxide solution, and the mixture was stirred at room temperature for five days. After removing the solvent by distillation, the residue was added with 9 ml of 1 N hydrochloric acid, and the mixture was extracted with 200 ml of ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and the solvent was evaporated, to give 320 mg of the title compound as pale yellow crystals.

Workup

  1. customAfter removing the solvent
  2. distillationby distillation
  3. additionthe residue was added with 9 ml of 1 N hydrochloric acid
  4. extractionthe mixture was extracted with 200 ml of ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-44f724fed735411d81e5e2fcd926e7e2
Source dataset
uspto-grants-2006_01
Patent number
US06982274B2

Reaction notes

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