Anthranilic Acid → 2-(1H-1,2,3,4-tetrazol-1-yl)benzoic acid
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]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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
- 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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