2-Amino-3-nitro-5-phenylpyridine → HCID 21882715, compound

HRID 722052Notes

Reaction equation

HRID 722052 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:4][N:3]=1>CO.[Pd]>[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:4][N:3]=1

Participants

4

Reactant 1

HCID 108225552-Amino-3-nitro-5-phenylpyridine2×

Product 1

HCID 21882715HCID 21882715, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

0.46 g of 2-amino-3-nitro-5-phenylpyridine (starting material C2) dissolved in 50 ml methanol are hydrogenated over 0.05 g of 10% strength Pd/C until no starting material is detectable by TLC. After filtration, the solvent is evaporated and the residue is chromatographed over silica gel (dichloromethane/methanol 20:1+1% triethylamine). Concentration of the pure fractions and drying in vacuo gives 0.38 g of the title compound as a brownish oil. The mass spectrum shows the molecular peak MH+ at 186.2 Da.

Workup

  1. filtrationAfter filtration
  2. customthe solvent is evaporated
  3. customthe residue is chromatographed over silica gel (dichloromethane/methanol 20:1+1% triethylamine)
  4. customConcentration of the pure fractions and drying in vacuo

Sources & evidence

ORD record
ord-d8cf6be093fc471d8e802fe7fcb045ac
Source dataset
uspto-grants-2006_11
Patent number
US07138399B2

Reaction notes

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