Ethyl orthoformate → HCID 57851532, compound

HRID 217331Notes

Reaction equation

HRID 217331 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-6d48b77d0b264f1aaa43737409852e2d
Source dataset
uspto-grants-2012_06
Patent number
US08193368B2

Reaction notes

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