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

Participants

Reaction Steps

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.

Provenance & Evidence