Ethyl orthoformate → HCID 57851532, compound

HRID 77752Notes

Reaction equation

HRID 77752 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[C:8]([N:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:11]2=[O:17])[CH:7]=[C:6]([NH2:18])[CH:5]=1.[N-:20]=[N+:21]=[N-:22].[Na+].[CH:24](OCC)(OCC)OCC>CC(O)=O>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:5]=[C:6]([N:18]2[CH:24]=[N:22][N:21]=[N:20]2)[CH:7]=[C:8]([N:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:11]2=[O:17])[CH:9]=1

Participants

5

Reactant 3

HCID 31214Ethyl orthoformateHCID 33557Sodium AzideHCID 57851670HCID 57851670, compound

Product 1

HCID 57851532HCID 57851532, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 3-Amino-5-(4-Methyl-2-oxo-2H-pyridin-1-yl)benzoic acid methyl ester (500 mg, 1.93 mmol) and NaN3 (233 g, 3.58 mmol) in AcOH was added HC(OEt)3 (1378.6 mg, 9.3 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-(4-Methyl-2-oxo-2H-pyridin-1-yl)-5-tetrazol-1-yl-benzoic acid methyl ester as a light yellow solid (602 mg, 100%). MS (M+H)=312.

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-dbadcb0f85104e1da8e570d923a8a907
Source dataset
uspto-grants-2014_09
Patent number
US08841336B2

Reaction notes

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