Sulfuric Acid → HCID 86704980, compound

HRID 572169Notes

Reaction equation

HRID 572169 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:19]3=[N:20][CH:21]=[CH:22][CH:23]=[C:18]3[C:17](=[O:24])[N:16]2[CH3:25])=[CH:11][CH:10]=1)C1C=CC=CC=1.S(=O)(=O)(O)O>O.[OH-].[Na+]>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([N:15]2[C:19]3=[N:20][CH:21]=[CH:22][CH:23]=[C:18]3[C:17](=[O:24])[N:16]2[CH3:25])=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 86704976HCID 86704976, compound

Product 1

HCID 86704980HCID 86704980, compoundYield 73.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 1-[4-(benzyloxy)phenyl]-2-methyl-1,2-dihydro-3H-pyrazolo[3,4-b]pyridin-3-one (0.28 g) obtained in Example 6, step D) and concentrated sulfuric acid (5.0 ml) was stirred at room temperature for 10 min. The obtained reaction mixture was diluted with water (10 ml), sodium hydroxide in m solid was added to pH 10, and the mixture was extracted with ethyl acetate. The organic layers were combined, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (0.15 g).

Workup

  1. customThe obtained reaction mixture
  2. additionwas added to pH 10
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-a89b6ac6658d4c9e90f8778cb9e4a73a
Source dataset
uspto-grants-2015_05
Patent number
US09029388B2

Reaction notes

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