Hydrazinecarboxaldehyde → 6-(2-Pyridyl)-1,2,4-triazolo[4,3-b]pyridazine

HRID 443513Notes

Reaction equation

HRID 443513 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:6][CH:7]=1.[CH:14]([NH:16][NH2:17])=O>C(O)CCC>[N:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[C:5]1[CH:6]=[CH:7][C:2]2[N:3]([CH:14]=[N:16][N:17]=2)[N:4]=1

Participants

4

Reactant 2

HCID 12229HydrazinecarboxaldehydeHCID 64179603-Chloro-6-(pyridin-2-yl)pyridazine

Product 1

HCID 234675766-(2-Pyridyl)-1,2,4-triazolo[4,3-b]pyridazine

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 1.0 g. of 3-chloro-6-(2-pyridyl)pyridazine and 0.6 g. of formic acid hydrazide in 50 ml. of n-butyl alcohol is heated at the reflux temperature for 18 hours. The volatiles are removed in vacuo and the residue is partitioned between dilute aqueous sodium hydroxide and methylene chloride. The organic layer is dried over sodium sulfate and filtered. The filtrate is evaporated and the residue is crystallized from methylene chloride-hexane to afford 1.0 g. of the desired product as off-white to yellow crystals, m.p. 191°-192° C.

Workup

  1. additionA mixture of 1.0 g
  2. customThe volatiles are removed in vacuo
  3. customthe residue is partitioned between dilute aqueous sodium hydroxide and methylene chloride
  4. dry with materialThe organic layer is dried over sodium sulfate
  5. filtrationfiltered
  6. customThe filtrate is evaporated
  7. customthe residue is crystallized from methylene chloride-hexane
  8. customto afford 1.0 g

Sources & evidence

ORD record
ord-e58587e3d57a455e90a9cbde34758b4a
Source dataset
uspto-grants-1981_04
Patent number
US04260756

Reaction notes

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