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

HRID 1763586Notes

Reaction equation

HRID 1763586 reaction equation
[CH3:1][C:2]1[N:6]2[N:7]=[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-])=O)[CH:12]=3)[CH:9]=[CH:10][C:5]2=[N:4][N:3]=1.FC(F)(F)C(O)=O.[H][H]>[Pd]>[NH2:17][C:13]1[CH:12]=[C:11]([C:8]2[CH:9]=[CH:10][C:5]3[N:6]([C:2]([CH3:1])=[N:3][N:4]=3)[N:7]=2)[CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12726840HCID 12726840, compoundHCID 178418361HCID 178418361, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 5.1 g. of 3-methyl-6-(m-nitrophenyl)-1,2,4-triazolo[4,3-b]pyridazine (prepared as in Example 23), 60 ml. of trifluoroacetic acid and 0.9 g. of 10% palladium catalyst on carbon is shaken in a Parr hydrogenator under about 35 pounds of hydrogen pressure until hydrogen uptake is complete. The catalyst is filtered off and the reaction mixture is concentrated. The residue is dissolved in water and adjusted to pH 5 by addition of 5N NaOH. The insoluble material is filtered off and washed with water to obtain 6-(m-aminophenyl)-3-methyl-1,2,4-triazolo[4,3-b]pyridazine, m.p. 193° C.

Workup

  1. additionA mixture of 5.1 g
  2. filtrationThe catalyst is filtered off
  3. concentrationthe reaction mixture is concentrated
  4. dissolutionThe residue is dissolved in water
  5. additionadjusted to pH 5 by addition of 5N NaOH
  6. filtrationThe insoluble material is filtered off
  7. washwashed with water

Sources & evidence

ORD record
ord-66039cda8ab14c3a94c3b36967662c6f
Source dataset
uspto-grants-1978_09
Patent number
US04112095

Reaction notes

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