3-Chloro-6-(3-nitrophenyl)pyridazine → 3-(Pyridazin-3-yl)aniline

HRID 1835439Notes

Reaction equation

HRID 1835439 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-])=O)[CH:9]=2)=[CH:6][CH:7]=1>[Pd].C(O)C>[N:3]1[CH:2]=[CH:7][CH:6]=[C:5]([C:8]2[CH:9]=[C:10]([NH2:14])[CH:11]=[CH:12][CH:13]=2)[N:4]=1

Participants

4

Reactant 1

HCID 122575043-Chloro-6-(3-nitrophenyl)pyridazine

Product 1

HCID 136348303-(Pyridazin-3-yl)anilineYield 62.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 3-chloro6-(3-nitro-phenyl)pyridazine (0.34 g) in tetrhydrofuran (5 ml) and ethanol (5 ml) was hydrogenated over palladium on carbon (10% w/w, 50% wet, 100 mg) under hydrogen atmosphere for 10 hours. The catalyst was filtered off and the filtrate was evaporated under reduced pressure. The residue was diluted with ethyl acetate and an aqueous solution of sodium hydrogen carbonate. The separated organic layer was washed with brine, dried over magnesium sulfate and evaporated under reduced pressure to give 3-pyridazin-3-yl-phenylamine (155 mg, 62.8%).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated under reduced pressure
  3. additionThe residue was diluted with ethyl acetate
  4. washThe separated organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-3c056d4085a947dc94bd13015ba5bc34
Source dataset
uspto-grants-2004_08
Patent number
US06770667B1

Reaction notes

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