Stannous Chloride → 3-(6-Chloropyridazin-3-yl)aniline

HRID 1906819Notes

Reaction equation

HRID 1906819 reaction equation
[Cl:1][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.[Sn](Cl)Cl>C(O)C>[Cl:1][C:2]1[N:3]=[N:4][C:5]([C:8]2[CH:9]=[C:10]([NH2:14])[CH:11]=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 122575043-Chloro-6-(3-nitrophenyl)pyridazine

Product 1

HCID 142802953-(6-Chloropyridazin-3-yl)anilineYield 50.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 50.0 g of 3-chloro-6-(3-nitrophenyl)pyridazine, 160.8 g tin dichloride and 1000 ml ethanol was refluxed for 1.0 hr, then cooled and approximately 1/2 of the soluent removed by evaporation under reduced pressure. The reaction mixture was added to 2.5 liters saturated aqueous sodium bicarbonate solution. After adjusting the pH to ~8 with additional sodium bicarbonate, 1.2 liters of methylene chloride was added and stirring continued. The resulting mixture was filtered and the salts washed repeatedly with methylene chloride and ethyl acetate. All organic fractions were then combined, dried (MgSO4) and the solvent removed in vacuo, to give 22 g of solid product, mp 118°-121° C.

Workup

  1. temperaturewas refluxed for 1.0 hr
  2. temperaturecooled
  3. customapproximately 1/2 of the soluent removed by evaporation under reduced pressure
  4. additionThe reaction mixture was added to 2.5 liters saturated aqueous sodium bicarbonate solution
  5. additionwas added
  6. filtrationThe resulting mixture was filtered
  7. washthe salts washed repeatedly with methylene chloride and ethyl acetate
  8. dry with materialdried (MgSO4)
  9. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-37e39cb98d9641b7a078884bbeb27181
Source dataset
uspto-grants-1987_03
Patent number
US04654343

Reaction notes

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