Ethyl orthoformate → 7-(2-Pyridinyl)-1,2,4-triazolo[4,3-a]pyridine

HRID 465122Notes

Reaction equation

HRID 465122 reaction equation
[NH:1]([C:3]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[CH:6]=[CH:5][N:4]=1)[NH2:2].[CH:15](OCC)(OCC)OCC>>[N:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:7]1[CH:6]=[CH:5][N:4]2[CH:15]=[N:2][N:1]=[C:3]2[CH:8]=1

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 135337172'-Hydrazino-2,4'-bipyridine

Product 1

HCID 135337087-(2-Pyridinyl)-1,2,4-triazolo[4,3-a]pyridine

Procedure

A mixture of 2.0 g of 2'-hydrazino-2,4'-bipyridine and 50 ml of triethyl orthoformate was heated on a steam bath for 18 hours then chilled and filtered. The crystals were dissolved in methylene chloride, treated with activated carbon, filtered and the filtrate concentrated. Chilling and filtration gave 1.5 g of the desired product as cream colored crystals, mp 144-°145° C.

Workup

  1. temperaturewas heated on a steam bath for 18 hours
  2. temperaturethen chilled
  3. filtrationfiltered
  4. dissolutionThe crystals were dissolved in methylene chloride
  5. additiontreated with activated carbon
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated
  8. temperatureChilling
  9. filtrationfiltration

Sources & evidence

ORD record
ord-1ff8877b5ac34ea2b3950340a906c49d
Source dataset
uspto-grants-1985_10
Patent number
US04550166

Reaction notes

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