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

HRID 2378714Notes

Reaction equation

HRID 2378714 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-(1H-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-b547c851bf7048e99d1d8b9f3f0fef03
Source dataset
uspto-grants-2008_12
Patent number
US07470717B2

Reaction notes

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