Sodium Hydroxide → 2-(1H-1,2,3,4-tetrazol-5-yl)benzoic acid

HRID 976579Notes

Reaction equation

HRID 976579 reaction equation
[N:1]1[NH:2][N:3]=[N:4][C:5]=1[C:6]1[CH:16]=[CH:15][CH:14]=[CH:13][C:7]=1[C:8]([O:10]CC)=[O:9].[OH-].[Na+]>C(O)C>[N:4]1[NH:3][N:2]=[N:1][C:5]=1[C:6]1[CH:16]=[CH:15][CH:14]=[CH:13][C:7]=1[C:8]([OH:10])=[O:9]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 583755ethyl 2-(2H-tetrazol-5-yl)benzoate

Product 1

HCID 5551922-(1H-1,2,3,4-tetrazol-5-yl)benzoic acidYield 0.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 2-cyanobenzoate (0.124 moles, 20.0 g) was dissolved in 55 g tributyltinazide and heated at 85° C. for 72 hours. The solution was allowed to cool. Methanol (200 ml) and water (50 ml) were added. The solution was stirred for 1 hour. Ethyl acetate and brine were added. The organic layer was dried and evaporated. The residue was triturated 3 times with large volumes of hexane, dissolved in chloroform, and precipitated with hexane. The precipitate was filtered to yield 10.0 g of ethyl 2-(2H-tetrazol-5-yl)benzoate. The ester (6.8 moles, 1.4 g) was dissolved in 5 ml ethanol and 10 ml of 2N NaOH added and heated on a steam bath for 1 hour. The solvent was removed under vacuum. The residue was dissolved in water. The pH was adjusted to 2.0 using 2N HCl. The intermediate was extracted with ethyl acetate to yield 0.8 g of 2-(2H-tetrazol-5-yl)benzoic acid.

Workup

  1. temperatureheated on a steam bath for 1 hour
  2. customThe solvent was removed under vacuum
  3. dissolutionThe residue was dissolved in water
  4. extractionThe intermediate was extracted with ethyl acetate

Sources & evidence

ORD record
ord-c4be0931149e45bf93a0766ff6fc6ef0
Source dataset
uspto-grants-1997_03
Patent number
US05612360

Reaction notes

Loading…