Ethyl orthoformate → 3-(5-Methyl-pyridin-2-yl)-5-tetrazol-1-yl-benzoic acid methyl ester

HRID 217327Notes

Reaction equation

HRID 217327 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][N:11]=2)[CH:7]=[C:6]([NH2:17])[CH:5]=1.[N-:19]=[N+:20]=[N-:21].[Na+].[CH:23](OCC)(OCC)OCC>CC(O)=O>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:5]=[C:6]([N:17]2[CH:23]=[N:21][N:20]=[N:19]2)[CH:7]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][N:11]=2)[CH:9]=1

Participants

5

Reactant 3

HCID 31214Ethyl orthoformateHCID 33557Sodium AzideHCID 57851018Methyl 3-amino-5-(5-methylpyridin-2-yl)benzoate

Product 1

HCID 578509943-(5-Methyl-pyridin-2-yl)-5-tetrazol-1-yl-benzoic acid methyl esterYield 100%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 3-amino-5-(5-methyl-pyridin-2-yl)-benzoic acid methyl ester (362 mg, 1.51 mmol) and NaN3 (182 g, 2.8 mmol) in AcOH was added HC(OEt)3 (1074 mg, 7.25 mmol) at room temperature. The reaction mixture was heated to reflux for 4 hours and then cooled to room temperature. The solvent was removed in vacuo and the residue was purified by silica-gel chromatography to give 3-(5-methyl-pyridin-2-yl)-5-tetrazol-1-yl-benzoic acid methyl ester as a light yellow solid (440 mg, 100%). MS (M+H)=296.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 4 hours
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by silica-gel chromatography

Sources & evidence

ORD record
ord-f5766d6344194a3f87c769b6bf0481d0
Source dataset
uspto-grants-2012_06
Patent number
US08193368B2

Reaction notes

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