Anthranilic Acid → 2-(5-methyl-1H-tetrazol-1-yl)benzoic acid

HRID 432695Notes

Reaction equation

HRID 432695 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].C(O[C:15](=O)[CH3:16])(=O)C.[N-:18]=[N+:19]=[N-:20].[Na+].Cl>[OH-].[Na+].C(O)(=O)C>[CH3:16][C:15]1[N:1]([C:2]2[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])[N:20]=[N:19][N:18]=1

Participants

7

Reactant 4

HCID 227Anthranilic AcidHCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 33557Sodium Azide

Product 1

HCID 125241922-(5-methyl-1H-tetrazol-1-yl)benzoic acidYield 87.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 14798Sodium HydroxideSolvent

Procedure

Under a nitrogen atmosphere, a solution of 2-aminobenzoic acid (100.0 g, 0.73 mol) in acetic anhydride (400 ml, 4.2 mol) was heated to reflux for 2 hours. The reaction was cooled to room temperature and the solvent was removed in vacuo. The residue was dissolved in glacial acetic acid (500 ml) and NaN3 (49.77 g, 0.77 mol) was added. The mixture was stirred overnight at room temperature followed by concentration of the acetic acid in vacuo. The residue was dissolved in 10% NaOH (500 ml) solution and heated to reflux for 3.5 hours. The reaction was cooled to room temperature and then poured over a mixture of ice water (2 L) and HCl (150 ml). A white solid precipitated and was collected by vacuum filtration. The solid was dried in vacuo to yield 130.5 g of 2-(5-methyl-1H-tetrazol-1-yl)benzoic acid.

Workup

  1. temperatureto reflux for 2 hours
  2. customthe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in glacial acetic acid (500 ml)
  4. temperatureheated
  5. temperatureto reflux for 3.5 hours
  6. temperatureThe reaction was cooled to room temperature
  7. customA white solid precipitated
  8. filtrationwas collected by vacuum filtration
  9. customThe solid was dried in vacuo

Sources & evidence

ORD record
ord-039aaed079db4a71879948c858bc0d63
Source dataset
uspto-grants-2003_12
Patent number
US06664260B2

Reaction notes

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