2-Amino-3-nitro-5-(2-methylpropyl)pyridine → 2,3-Diamino-5-(2-methylpropyl)pyridine

HRID 722053Notes

Reaction equation

HRID 722053 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][C:5]([CH2:11][CH:12]([CH3:14])[CH3:13])=[CH:4][N:3]=1>CO.[Pd]>[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([CH2:11][CH:12]([CH3:14])[CH3:13])=[CH:4][N:3]=1

Participants

4

Reactant 1

HCID 218827302-Amino-3-nitro-5-(2-methylpropyl)pyridine2×

Product 1

HCID 218827102,3-Diamino-5-(2-methylpropyl)pyridineYield 87.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

0.46 g of 2-amino-3-nitro-5-(2-methylpropyl)pyridine (starting material D2) dissolved in 20 ml of 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 25:1). Concentration of the pure fractions and drying in vacuo gives 0.34 g of the title compound as an oil. The mass spectrum shows the molecular peak MH+ at 166.2 Da.

Workup

  1. filtrationAfter filtration
  2. customthe solvent is evaporated
  3. customthe residue is chromatographed over silica gel (dichloromethane/methanol 25:1)
  4. customConcentration of the pure fractions and drying in vacuo

Sources & evidence

ORD record
ord-e28a9d04c2e443f0bf6b24b53ff96b7c
Source dataset
uspto-grants-2006_11
Patent number
US07138399B2

Reaction notes

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