Hydrazine → HCID 11437307, compound

HRID 446169Notes

Reaction equation

HRID 446169 reaction equation
NN.[N:3]1([N:8]([C:18]2[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=2)[C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)[CH:7]=[CH:6][N:5]=[CH:4]1>C(O)C.[Ru]>[NH2:15][C:12]1[CH:11]=[CH:10][C:9]([N:8]([C:18]2[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=2)[N:3]2[CH:7]=[CH:6][N:5]=[CH:4]2)=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 11381181HCID 11381181, compound

Product 1

HCID 11437307HCID 11437307, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 23950RutheniumCatalystHCID 702EthanolSolvent

Procedure

Hydrazine (1.52 ml, 49.00 mmol) was added portionwise to a suspension of 4-[N-(1H-imidazol-1-yl)-N-(4-nitrophenyl)amino]benzonitrile (3.00 g, 9.80 mM) and ruthenium, 5 wt. % on carbon (0.30 g, 0.15 mM) in ethanol (35 ml) at reflux with stirring. When TLC showed complete reaction, the mixture was cooled and the catalyst was filtered. The solvent was concentrated under vacuum. The residue was poured into water and extracted with dichloromethane, dried over Na2SO4, filtered, and concentrated under vacuum to give the crude product (2.50 g as solid). Crystallization from ethyl acetate with ethanol yielded the expected product (1.30 g, 50%, mp: 147° C.).

Workup

  1. temperatureat reflux
  2. customreaction
  3. temperaturethe mixture was cooled
  4. filtrationthe catalyst was filtered
  5. concentrationThe solvent was concentrated under vacuum
  6. additionThe residue was poured into water
  7. extractionextracted with dichloromethane
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated under vacuum
  11. customto give the crude product (2.50 g as solid)
  12. customCrystallization from ethyl acetate with ethanol

Sources & evidence

ORD record
ord-69edd1c6a2d4433d8843384183563505
Source dataset
uspto-grants-2013_07
Patent number
US08476455B2

Reaction notes

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