Water → 5-(Aminomethyl)-2-chloropyridine
Reaction equation
O.NN.[Cl:4][C:5]1[N:10]=[CH:9][C:8]([CH2:11][N:12]2C(=O)C3=CC=CC=C3C2=O)=[CH:7][CH:6]=1.O>CCO>[Cl:4][C:5]1[N:10]=[CH:9][C:8]([CH2:11][NH2:12])=[CH:7][CH:6]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Hydrazine hydrate (1.7 ml) was added to a refluxing solution of 6.5 g (2.4×10-2 mole) of N-(6-chloro-3-pyridylmethyl)phthalimide in 100 ml of EtOH, and the mixture was further refluxed for 1 hour. After addition of 20 ml of water, the ethanol was distilled off under reduced pressure. Concentrated hydrochloric acid (25 ml) was added to the residue and the mixture was refluxed for 1 hour. After cooling, the reaction mixture was neutralized with NaOH and the aqueous layer was saturated with NaCl and extracted with Et2O. The extract was dried over Na2SO4 and the solvent was distilled off to give 2.4 g of the title compound as a yellow oil.