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

HRID 465115Notes

Reaction equation

HRID 465115 reaction equation
[NH:1]([C:3]1[C:8]([C:9]2[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=2)=[CH:7][CH:6]=[CH:5][N:4]=1)[NH2:2].[CH:15](OCC)(OCC)OCC>>[N:11]1[CH:12]=[CH:13][CH:14]=[C:9]([C:8]2[C:3]3[N:4]([CH:15]=[N:2][N:1]=3)[CH:5]=[CH:6][CH:7]=2)[CH:10]=1

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 135337152-Hydrazino-3,3'-bipyridine

Product 1

HCID 135337048-(3-Pyridinyl)-1,2,4-triazolo[4,3-a]pyridine

Conditions

Temperature
100 °C

Procedure

A 4.15 g portion of 2-hydrazino-3,3'-bipyridine was dissolved in 30 ml of triethyl orthoformate and heated at 100° C. for 2 hours. The volatiles were removed at reduced pressure and the residue purified by chromatography on hydrous magnesium silicate, eluting with ethyl acetate. The solid was recrystallized from methylene chloride-hexane, giving 2.67 g of the desired product, mp 186°-189° C.

Workup

  1. customThe volatiles were removed at reduced pressure
  2. customthe residue purified by chromatography on hydrous magnesium silicate
  3. washeluting with ethyl acetate
  4. customThe solid was recrystallized from methylene chloride-hexane

Sources & evidence

ORD record
ord-db9af6fd3a9f4d898db18d8f8c613664
Source dataset
uspto-grants-1985_10
Patent number
US04550166

Reaction notes

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