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

HRID 465132Notes

Reaction equation

HRID 465132 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 mixture of 0.27 g of 2'-hydrazino-3,3'-bipyridine and 5 ml of triethyl orthoacetate was heated at 130° C. for 1.5 hours and the solvent removed. The residue was chromatographed on silica gel and eluted first with ethyl acetate:methanol (9:2), then with methanol to elute the product. This solid was recrystallized from methylene chloride-hexane giving the desired product as tan crystals, mp 112°-115° C.

Workup

  1. customthe solvent removed
  2. customThe residue was chromatographed on silica gel
  3. washeluted first with ethyl acetate:methanol (9:2)
  4. washwith methanol to elute the product
  5. customThis solid was recrystallized from methylene chloride-hexane giving the desired product as tan crystals, mp 112°-115° C.

Sources & evidence

ORD record
ord-b55d5389872e4e189ca036ad506a6b64
Source dataset
uspto-grants-1985_10
Patent number
US04550166

Reaction notes

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