HCID 54166861, compound → HCID 54069952, compound

HRID 1451377Notes

Reaction equation

HRID 1451377 reaction equation
CN(C)[CH:3]=[CH:4][C:5]1[C:10]([N+:11]([O-])=O)=[CH:9][N:8]=[C:7]([N:14]2[CH:18]=[N:17][CH:16]=[N:15]2)[CH:6]=1.[H][H]>C(O)C.[Pt]=O>[N:14]1([C:7]2[CH:6]=[C:5]3[CH:4]=[CH:3][NH:11][C:10]3=[CH:9][N:8]=2)[CH:18]=[N:17][CH:16]=[N:15]1

Participants

5

Reactant 2

HCID 54166861HCID 54166861, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54069952HCID 54069952, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

N,N-Dimethyl-2-(5-nitro-2-(1,2,4-triazol-1-yl)pyridin-4-yl)ethenamine (8 g, 31 mmol) was hydrogenated over platinum oxide (1.6 g) in ethanol (150 mL) at 30 psi of hydrogen for 1 hour. The catalyst was removed by filtration and the solvent evaporated in vacuo. The residue was chromatographed on silica eluting with ethyl acetate to afford an orange/brown solid. This was triturated with ether and the precipitate collected by filtration to give the title compound (2.89 g, 51%) as a pink solid. mp 203°-205° C. 1H NMR (360 MHz, d6 -DMSO)δ6.67 (1H, d, J=3.0 Hz), 7.76 (1H, d, J=2.9 Hz), 8.01 (1H, s), 8.23 (1H, s), 8.70 (1H, s), 9.25 (1H, s) and 11.86 (1H, br s).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent evaporated in vacuo
  3. customThe residue was chromatographed on silica eluting with ethyl acetate
  4. customto afford an orange/brown solid
  5. customThis was triturated with ether
  6. filtrationthe precipitate collected by filtration

Sources & evidence

ORD record
ord-fbe29a63e8664f358b4137d3af7bc7d5
Source dataset
uspto-grants-1997_02
Patent number
US05604240

Reaction notes

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