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

HRID 857711Notes

Reaction equation

HRID 857711 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-ed445606220a47f8806c6dc2489225c9
Source dataset
uspto-grants-2006_12
Patent number
US07144899B2

Reaction notes

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