Ethyl orthoformate → 6-Tetrazol-1-yl-pyridin-3-ol

HRID 407942Notes

Reaction equation

HRID 407942 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[NH2:5][C:6]1[N:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.[CH2:13](OC(OCC)OCC)C>CC(O)=O>[N:5]1([C:6]2[N:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=2)[CH:13]=[N:3][N:2]=[N:1]1

Participants

5

Reactant 3

HCID 31214Ethyl orthoformateHCID 33557Sodium AzideHCID 42319722-Amino-5-hydroxypyridine

Product 1

HCID 577084326-Tetrazol-1-yl-pyridin-3-olYield 81%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of sodium azide (2.90 g, 44 mmol) in triethylorthoformate (8 mL) and AcOH (50 mL) was added 6-amino-pyridine-3-ol (3.5 g, 32 mmol). The reaction was heated to 100° C. for 6 hours and then cooled to ambient temperature and allowed to stir overnight. The solids were filtered, washed with EtOAc and dried in vacuo to give the 6-(1H-tetrazol-1-yl)pyridin-3-ol (4.20 g, 81%) as a beige solid.

Workup

  1. temperaturecooled to ambient temperature
  2. filtrationThe solids were filtered
  3. washwashed with EtOAc
  4. customdried in vacuo

Sources & evidence

ORD record
ord-94c16cba742a4999bd81b04f4eb20243
Source dataset
uspto-grants-2014_06
Patent number
US08754226B2

Reaction notes

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