Triethyl orthoacetate → 3-Methyl-8-(3-pyridinyl)-1,2,4-triazolo[4,3-a]pyridine

HRID 465114Notes

Reaction equation

HRID 465114 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].[C:15](OCC)(OCC)(OCC)[CH3:16]>>[CH3:15][C:16]1[N:4]2[CH:5]=[CH:6][CH:7]=[C:8]([C:9]3[CH:10]=[N:11][CH:12]=[CH:13][CH:14]=3)[C:3]2=[N:1][N:2]=1

Participants

3

Reactant 2

HCID 66221Triethyl orthoacetateHCID 135337152-Hydrazino-3,3'-bipyridine

Product 1

HCID 135337033-Methyl-8-(3-pyridinyl)-1,2,4-triazolo[4,3-a]pyridine

Conditions

Temperature
130 °C

Procedure

A 1.0 g portion of 2-hydrazino-3,3'-bipyridine was dissolved in 5 ml of triethyl orthoacetate and heated at 130° C. for 1.5 hours. The volatiles were removed at reduced pressure and the residue purified by chromatography on silica gel, eluting with ethyl acetate:methanol (9:2). The resulting solid was recrystallized from methylene chloride-hexane, giving the desired product as a tan powder, mp 112.5°-115° C.

Workup

  1. customThe volatiles were removed at reduced pressure
  2. customthe residue purified by chromatography on silica gel
  3. washeluting with ethyl acetate:methanol (9:2)
  4. customThe resulting solid was recrystallized from methylene chloride-hexane

Sources & evidence

ORD record
ord-31cc758f1c994e97b80e132e38ea0bdd
Source dataset
uspto-grants-1985_10
Patent number
US04550166

Reaction notes

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