5-(4-Chlorophenyl)-2-hydrazinopyridine → 6-(4-Chlorophenyl)-3-methyl-1,2,4-triazolo[4,3-a]pyridine

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]([NH:14][NH2:15])=[N:12][CH:13]=2)=[CH:4][CH:3]=1.[C:16]([O-])([O-])(OCC)[CH3:17]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]([C:16]([CH3:17])=[N:15][N:14]=3)[CH:13]=2)=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 203000925-(4-Chlorophenyl)-2-hydrazinopyridine

HCID 86598186Ethyl ortho-acetate

Product 1

HCID 203000986-(4-Chlorophenyl)-3-methyl-1,2,4-triazolo[4,3-a]pyridine

Procedure

A mixture of 8.5 g. of 5-(4-chlorophenyl)-2-hydrazinopyridine and 80 ml. of ethyl orthoacetate is refluxed for 5 hours, the mixture is filtered and the solid is washed with hexane to afford 5.0 g. of the product of the Example as a tan solid, m.p. 192°-193.5° C.

Workup

additionA mixture of 8.5 g
filtrationthe mixture is filtered
washthe solid is washed with hexane
customto afford 5.0 g

Sources & evidence

ORD record: ord-741fdbed7f9a4dbfa7c1801cfccdb982
Source dataset: uspto-grants-1980_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04242515

Reaction notes

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