Ethyl orthoformate → 8-(Benzyloxy)-[1,2,4]triazolo[4,3-a]pyridine

HRID 1809641Notes

Reaction equation

HRID 1809641 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([NH:15][NH2:16])=[N:11][CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:17](OC(OCC)OCC)C>>[CH2:1]([O:8][C:9]1[C:10]2[N:11]([CH:17]=[N:16][N:15]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 674857313-(Benzyloxy)-2-hydrazinopyridine

Product 1

HCID 205193998-(Benzyloxy)-[1,2,4]triazolo[4,3-a]pyridineYield 76.8%

Procedure

A flask was charged with 3-(benzyloxy)-2-hydrazinylpyridine (10.0 g, 46.5 mmol) and triethoxymethane (77.3 ml, 465 mmol). The mixture was heated at reflux for 1 hour and then stirred overnight at ambient temperature. The solids were filtered and rinsed with EtOH and dried on high vacuum to afford 8-(benzyloxy)-[1,2,4]triazolo[4,3-a]pyridine (8.05 g, 35.7 mmol, 76% yield).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1 hour
  3. filtrationThe solids were filtered
  4. washrinsed with EtOH
  5. customdried on high vacuum

Sources & evidence

ORD record
ord-89de51990db6481583aa5152dd2b146a
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Reaction notes

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