Hydrazine hydrate (1:1) → HCID 16641866, compound

HRID 1023529Notes

Reaction equation

HRID 1023529 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[O:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][N:11]=1.O.NN>C(O)C.[Pd]>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[O:9][C:10]1[N:11]=[CH:12][C:13]([NH2:16])=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 24623396HCID 24623396, compound2×

Product 1

HCID 16641866HCID 16641866, compoundYield 88.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-[(2,5-dimethylphenyl)oxy]-5-nitropyridine (Intermediate 33, 140 mg, 0.450 mmol) was dissolved in ethanol (3 mL). Hydrazine hydrate (83 μL, 0.884 mmol) and palladium on carbon (47 mg, 0.044 mmol) were added. The reaction mixture was heated at reflux under argon. After overnight heating, the reaction was cooled down. The reaction mixture was filtered. The organic phase was evaporated under vacuum. The residue was purified by SCX (wash with MeOH, desorbed with 2N methanolic ammonia). Evaporation afforded the title compound (85 mg).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux under argon
  3. temperatureAfter overnight heating
  4. temperaturethe reaction was cooled down
  5. filtrationThe reaction mixture was filtered
  6. customThe organic phase was evaporated under vacuum
  7. customThe residue was purified by SCX (wash with MeOH, desorbed with 2N methanolic ammonia)
  8. customEvaporation

Sources & evidence

ORD record
ord-15e424a75c92465cac059aff32d64a8c
Source dataset
uspto-grants-2014_05
Patent number
US08722695B2

Reaction notes

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