Ammonia → HCID 14998298, compound

HRID 1896466Notes

Reaction equation

HRID 1896466 reaction equation
Cl[C:2]1[CH:3]=[C:4]([CH3:17])[C:5]2[N:6]([C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[N:9][N:10]=2)[N:7]=1.N>C(O)C.[Pd]>[CH3:17][C:4]1[C:5]2[N:6]([C:8]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)=[N:9][N:10]=2)[N:7]=[CH:2][CH:3]=1

Participants

5

Reactant 2

HCID 222AmmoniaHCID 14998306HCID 14998306, compound

Product 1

HCID 14998298HCID 14998298, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

6-chloro-8-methyl-3-phenyl[1,2,4]triazolo[4,3-b]pyridazine x240 is dissolved in ethanol (300 ml), and 10% Pd/C (0.9 g) and 25% aqueous ammonia (60 ml) are added. The mixture is hydrogenated in the Parr apparatus under hydrogen pressure 2.5 atm at room temperature for 1h10. The reaction mixture is filtered through a Celite layer, which is washed with ethanol. The combined filtrates are evaporated, and the residue is dissolved in dichloromethane. The solution is washed with brine and dried over anhydrous Na2SO4. The solvent is removed under reduced pressure to afford 2.9 g of 8-methyl-3-phenyl[1,2,4]triazolo[4,3-b]pyridazine x241.

Workup

  1. customat room temperature
  2. filtrationThe reaction mixture is filtered through a Celite layer, which
  3. washis washed with ethanol
  4. customThe combined filtrates are evaporated
  5. dissolutionthe residue is dissolved in dichloromethane
  6. washThe solution is washed with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-cb605a9971e549909f0973e6465f44bc
Source dataset
uspto-grants-2013_08
Patent number
US08518943B2

Reaction notes

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