Ethanol → 3-Methyl-6-[3-(amino)phenyl]-1,2,4-triazolo[4,3-b]pyridazine

HRID 1906806Notes

Reaction equation

HRID 1906806 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[N:14]3[N:15]=C[CH:17]=[CH:18][C:13]3=[N:12][N:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O.NN.[CH2:21](O)[CH3:22]>[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([C:10]2[CH:17]=[CH:18][C:13]3[N:12]([C:21]([CH3:22])=[N:15][N:14]=3)[N:11]=2)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 9321HydrazineHCID 86741387HCID 86741387, compound

Product 1

HCID 127268683-Methyl-6-[3-(amino)phenyl]-1,2,4-triazolo[4,3-b]pyridazine

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
20 °C

Procedure

A 103.0 g portion of 3-methyl-6-(3-nitrophenyl-1,2,4-triazolo[4,3-b]pyridazine and 1.0 g of 10% palladium on carbon were suspended in 2 liters of ethanol. The mixture was heated to reflux and 140 ml of anhydrous hydrazine added via a syringe pump over 24 hours. The solution was cooled to 20° C., filtered and the filtrate concentrated in vacuo. The residue was dissolved in 3 liters of hot dichloromethane and passed through a short column (200 g) of hydrous magnesium silicate with dichloromethane as the eluent. The fractions containing product were combined and evaporated, giving 83 g of the desired compound as yellow needles, mp 206°-208° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated in vacuo
  5. dissolutionThe residue was dissolved in 3 liters of hot dichloromethane
  6. additionThe fractions containing product
  7. customevaporated

Sources & evidence

ORD record
ord-9976b5583afb494ea5ad927e2a505f20
Source dataset
uspto-grants-1987_03
Patent number
US04654343

Reaction notes

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