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

HRID 80639Notes

Reaction equation

HRID 80639 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].C(OC([O:12][CH2:13][CH3:14])OCC)C.[NH2:15][C:16]1[N:21]=[CH:20]C(O)=[CH:18][CH:17]=1>CC(O)=O>[N:21]1([C:16]2[N:15]=[CH:14][C:13]([OH:12])=[CH:18][CH:17]=2)[CH:20]=[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-ol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

NaN3 (2.89 g, 44 mmol) and triethylorthoformate (7.4 ml, 44 mmol) were added to commercially available 6-amino-pyridin-3-ol (3.5 g, 32 mmol) in AcOH (50 mL). The reaction mixture was heated to 100° C. for 1-3 hours. The reaction was cooled to room temperature and left to stand overnight. The precipitate was filtered, washed with EtOAc (150 mL) and dried in vacuo. The crude product was obtained as a beige solid and used in the next step without further purification.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. waitleft
  3. filtrationThe precipitate was filtered
  4. washwashed with EtOAc (150 mL)
  5. customdried in vacuo

Sources & evidence

ORD record
ord-832749ce1eed4c72b6729c65b4a36f0d
Source dataset
uspto-grants-2014_09
Patent number
US08846675B2

Reaction notes

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