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

HRID 1928590Notes

Reaction equation

HRID 1928590 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-e334b9dea03d4ab796ae954b007b83a0
Source dataset
uspto-grants-2012_05
Patent number
US08183381B2

Reaction notes

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