Trimethyl orthoformate → 5-Chloro-2-(1H-tetrazol-1-yl)benzoic acid

HRID 857715Notes

Reaction equation

HRID 857715 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH:12](OC)(OC)OC.[N-:19]=[N+:20]=[N-:21].[Na+]>C(O)(=O)C>[Cl:11][C:8]1[CH:9]=[CH:10][C:2]([N:1]2[CH:12]=[N:21][N:20]=[N:19]2)=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 9005Trimethyl orthoformateHCID 124762-Amino-5-chlorobenzoic acidHCID 33557Sodium Azide

Product 1

HCID 117155615-Chloro-2-(1H-tetrazol-1-yl)benzoic acidYield 62%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A suspension of 2-amino-5-chloro-benzoic acid (5.0 g, 0.029 mol), trimethyl orthoformate (9.5 mL, 0.087 mol) and sodium azide (5.6 g, 0.087 mol) in glacial acetic acid (105 mL) was stirred at room temperature for 2 h. Filtration and concentration from toluene gave 5-chloro-2-(1H-tetraazol-1-yl)benzoic acid (4.0 g, 62%); 1H NMR (400 MHz, CD3OD): δ 9.47 (s, 1H), 8.16 (d, J=2.5 Hz, 1H), 7.83 (dd, J=2.5, 8.5 Hz, 1H), 7.62 (d, J=8.5 Hz, 1H).

Workup

  1. filtrationFiltration and concentration from toluene

Sources & evidence

ORD record
ord-ebf805073e75491ca120c7f871ee2006
Source dataset
uspto-grants-2006_12
Patent number
US07144899B2

Reaction notes

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