Anthranilic Acid → 2-(1H-1,2,3,4-tetrazol-1-yl)benzoic acid

HRID 1795260Notes

Reaction equation

HRID 1795260 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH:11](OC)(OC)OC.[N-:18]=[N+:19]=[N-:20].[Na+]>C(O)(=O)C>[N:1]1([C:2]2[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])[CH:11]=[N:20][N:19]=[N:18]1

Participants

5

Reactant 3

HCID 227Anthranilic AcidHCID 9005Trimethyl orthoformateHCID 33557Sodium Azide

Product 1

HCID 7536082-(1H-1,2,3,4-tetrazol-1-yl)benzoic acid

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A suspension of 2-aminobenzoic acid (6.0 g, 0.044 mol), trimethyl orthoformate (14.2 ml, 0.13 mol) and sodium azide (8.4 g, 0.13 mol) in glacial acetic acid (150 ml) was stirred at room temperature for 2 h. Filtration and concentration from toluene gave 2-tetrazol-1-yl-benzoic acid; 1H NMR (CD3OD, 400 MHz) δ 9.47 (s, 1H), 8.19 (dd, 1H, J=7.7 Hz, J=1.6 Hz), 7.79 (m, 2H), 7.61 (dd, 1H, J=7.7 Hz, J=1.5 Hz).

Workup

  1. filtrationFiltration and concentration from toluene

Sources & evidence

ORD record
ord-79feacfa0a1c4cc0be9d53bbba66e09f
Source dataset
uspto-grants-2006_04
Patent number
US07026324B2

Reaction notes

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