Methanol → 3-(5-methyl-1H-tetrazol-1-yl)pyridine-4-carboxylic acid

HRID 1823351Notes

Reaction equation

HRID 1823351 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]([OH:10])=[O:9].[N-:11]=[N+:12]=[N-:13].[Na+].CO.[C:17](OC(=O)C)(=O)[CH3:18]>>[CH3:17][C:18]1[N:1]([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][C:7]=2[C:8]([OH:10])=[O:9])[N:13]=[N:12][N:11]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 7918Acetic AnhydrideHCID 33557Sodium AzideHCID 4595313-Aminoisonicotinic acid

Product 1

HCID 221726643-(5-methyl-1H-tetrazol-1-yl)pyridine-4-carboxylic acid

Procedure

3-Aminopyridine-4-carboxylic acid (50.0 g, 0.36 mol) was suspended in acetic anhydride (250 mL) then heated at reflux for 2 hours. The reaction mixture was concentrated under vacuum. The solid residue was slurried with heptane then concentrated under vacuum. The resulting solid was covered with acetic acid (300 mL), then sodium azide (23.5 g, 0.36 mol) was added. The reaction exothermed to 50° C. The reaction mixture was allowed to stir at ambient temperature overnight. The precipitate was isolated by filtration then slurried with methanol and filtered. The solid was dissolved in 10% sodium hydroxide. The solution was heated on a steam bath for 30 minutes, allowed to cool to ambient temperature then neutralized with 6N hydrochloric acid. The resulting precipitate was isolated by filtration, washed with water and dried to provide 64.5 g of 3-(5-methyl-1H-tetrazol-1-yl)pyridine-4-carboxylic acid as an off white solid, m.p. 214–215° C. (decomposition).

Workup

  1. temperaturethen heated
  2. temperatureat reflux for 2 hours
  3. concentrationThe reaction mixture was concentrated under vacuum
  4. concentrationthen concentrated under vacuum
  5. customexothermed to 50° C
  6. customThe precipitate was isolated by filtration
  7. filtrationfiltered
  8. dissolutionThe solid was dissolved in 10% sodium hydroxide
  9. temperatureThe solution was heated on a steam bath for 30 minutes
  10. temperatureto cool to ambient temperature
  11. customThe resulting precipitate was isolated by filtration
  12. washwashed with water
  13. customdried

Sources & evidence

ORD record
ord-8abbb7245e4646989c5a8d8cd81fd3b8
Source dataset
uspto-grants-2006_05
Patent number
US07038051B2

Reaction notes

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