Hydrazine hydrate (1:1) → HCID 21882687, compound

HRID 722064Notes

Reaction equation

HRID 722064 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[C:6]([O:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:5]=[CH:4][N:3]=1.O.NN>[Ni].CO>[NH2:1][C:2]1[C:7]([NH2:8])=[C:6]([O:11][CH2:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 21882742HCID 21882742, compound

Product 1

HCID 21882687HCID 21882687, compoundYield 69.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1.11 g of 2-amino-4-(2-phenylethoxy)-3-nitropyridine (starting material K2), 1.0 ml of hydrazine hydrate and 0.130 g of Raney nickel in 30 ml of methanol is heated under reflux until no starting material is detectable by TLC. After filtration and evaporation of the solvent the residue is chromatographed on silica gel (dichloromethane/methanol 20:1+1% triethylamine). Concentration of the pure fractions and drying in vacuo gives 0.68 g of the title compound as an oil, which crystallizes on standing (m.p. 86–87° C.). The mass spectrum shows the molecular peak MH+ at 230.2 Da.

Workup

  1. temperatureis heated
  2. temperatureunder reflux until no starting material
  3. filtrationAfter filtration and evaporation of the solvent the residue
  4. customis chromatographed on silica gel (dichloromethane/methanol 20:1+1% triethylamine)
  5. customConcentration of the pure fractions and drying in vacuo

Sources & evidence

ORD record
ord-97611bd682ff4fc384c8b68084de495e
Source dataset
uspto-grants-2006_11
Patent number
US07138399B2

Reaction notes

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