Sodium Hydroxide → (E)-4-(2-(1H-indazol-3-yl)vinyl)benzoic acid

HRID 2075431Notes

Reaction equation

HRID 2075431 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:21]=[CH:20][C:15]([C:16]([O:18]C)=[O:17])=[CH:14][CH:13]=2)=[N:2]1.[OH-].[Na+]>CO>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[CH:11]/[C:12]2[CH:21]=[CH:20][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=2)=[N:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 11952156methyl (E)-4-[2-(1H-indazol-3-yl)vinyl]benzoate

Product 1

HCID 11437002(E)-4-(2-(1H-indazol-3-yl)vinyl)benzoic acidYield 104.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl (E)-4-[2-(H-indazol-3-yl)vinyl]benzoate (0.71 g, 2.54 mmol) obtained in Step 5 was dissolved in methanol (2.6 mL), and the solution was added with an aqueous sodium hydroxide solution (1 mol/L, 5.00 mL), followed by heating under reflux for 1.5 hours. Methanol was evaporated under reduced pressure, the pH of the residue was adjusted to 3 or below with 6 mol/L hydrochloric acid under ice-cooling. The resulting precipitates were collected by filtration to obtain (E)-4-[2-(1H-indazol-3-yl)vinyl]benzoic acid (0.70 g, quantitative yield).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 1.5 hours
  3. customMethanol was evaporated under reduced pressure
  4. temperaturecooling
  5. customThe resulting precipitates
  6. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-994a18ea12d540b1ba101b0d333a3f72
Source dataset
uspto-grants-2011_04
Patent number
US07919517B2

Reaction notes

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