Trifluoroacetic acid → HCID 178480755, compound

HRID 2236844Notes

Reaction equation

HRID 2236844 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[N:13]=[C:12]([OH:14])[C:11]([N+:15]([O-])=O)=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.FC(F)(F)C(O)=O.C(N(CC)CC)C>C(O)C>[NH2:15][C:11]1[C:12]([OH:14])=[N:13][C:8]([N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 178480757HCID 178480757, compound

Product 1

HCID 178480755HCID 178480755, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension 6-(4-methylpiperazin-1-yl)-3-nitropyridin-2-ol.trifluoroacetic acid salt (0.17 g, 0.48 mmol) in ethanol (25 mL) is added triethylamine dropwise with agitation until all of the solid had dissolved. The mixture is then degassed with dry ice and treated with an aqueous slurry of Raney nickel (approx 1 mL). After shaking under 50 psi of hydrogen, the reaction mixture is filtered through a pad of diatomaceous earth and concentrated under reduced pressure to give 3-amino-6-(4-methyl-piperazin-1-yl)-pyridin-2-ol (0.15 g, contaminated with triethylammonium trifluoroacetate) as a blue solid.

Workup

  1. dissolutionhad dissolved
  2. customThe mixture is then degassed with dry ice
  3. additiontreated with an aqueous slurry of Raney nickel (approx 1 mL)
  4. filtrationthe reaction mixture is filtered through a pad of diatomaceous earth
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-119abc3572654e4688e2b4e0dd09bf5b
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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