Trifluoroacetic acid → HCID 13424600, compound

HRID 462410Notes

Reaction equation

HRID 462410 reaction equation
[CH3:1][N:2]1[C:20](=[O:21])[N:5]2[N:6]=[C:7]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-])=O)[CH:12]=3)[C:8]([CH3:10])=[CH:9][C:4]2=[N:3]1.FC(F)(F)C(O)=O.[H][H]>[Pd]>[NH2:17][C:13]1[CH:12]=[C:11]([C:7]2[C:8]([CH3:10])=[CH:9][C:4]3[N:5]([C:20](=[O:21])[N:2]([CH3:1])[N:3]=3)[N:6]=2)[CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 13424599HCID 13424599, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13424600HCID 13424600, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 5.0 g of 2,7-dimethyl-6-(m-nitrophenyl)-1,2,4-triazolo[4,3-b]pyridazin-3(2H)-one, 50 ml. of trifluoroacetic acid and a catalytic amount of 10% palladium on carbon are shaken in a Parr bottle under 40 lb. pressure of hydrogen for 2 hours and then filtered. The filtrate is concentrated in vacuo to an oil which is dissolved in 50 ml. of water and adjusted to pH 4.7 with 5N sodium hydroxide. The resulting solid is collected by filtration and air dried, giving 3.6 g. of the desired product as a green solid, m.p. 192°-195° C.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate is concentrated in vacuo to an oil which
  3. dissolutionis dissolved in 50 ml
  4. filtrationThe resulting solid is collected by filtration and air
  5. customdried
  6. customgiving 3.6 g

Sources & evidence

ORD record
ord-abe22ec3735646148ae84c29c335f574
Source dataset
uspto-grants-1985_05
Patent number
US04515791

Reaction notes

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