Hydrazine hydrate (1:1) → HCID 21882714, compound

HRID 722066Notes

Reaction equation

HRID 722066 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-])=O)=[C:6]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=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][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 21882700HCID 21882700, compound

Product 1

HCID 21882714HCID 21882714, compoundYield 85.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 0.88 g of 2-amino-4-benzyloxy-3-nitropyridine (starting material M2), 0.81 ml of hydrazine hydrate and 0.100 g of Raney nickel in 25 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 0.66 g of the title compound as a brownish solid of m.p. 135–136° C. The mass spectrum shows the molecular peak MH+ at 216.1 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-e2c8f19fcebe4cbe89d945450fa0fe89
Source dataset
uspto-grants-2006_11
Patent number
US07138399B2

Reaction notes

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