HCID 54166861, compound → HCID 54069952, compound

HRID 1459732Notes

Reaction equation

HRID 1459732 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 (150ml) at 30 psi of hydrogen for 1 h. The catalyst was removed by filtration and the solvent evaporated in uacuo. 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) δ 6.67 (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), 11.86 (1H, br s).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent evaporated in uacuo
  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-07a2031df2904271bdf93652152f9eed
Source dataset
uspto-grants-1998_12
Patent number
US05854268

Reaction notes

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