Phthalazine → 1,2-Phenylenedimethanamine

Participants

Reaction Steps

Phthalazine (21.5 g, 0.165 mol), 10% palladium on carbon (2 g), and methanol (125 mL) were combined in a pressure bottle and shaken at room temperature under 60 psi of hydrogen for 5 days. Raney-nickel® slurry (6.42 g) and 10% palladium on carbon (0.50 g) were added, and the mixture was shaken at 50° C. under 60 psi of hydrogen for 16 hours. The mixture was filtered through a nylon membrane and concentrated to give the titled compound: 1H NMR (300 MHz, DMSO-d6) δ ppm 7.32 (dd, J=5.4, 3.5 Hz, 2H), 7.17 (dd, J=5.6, 3.4 Hz, 2H), 3.74 (s, 4H); MS (DCI/NH3) m/z 137 (M+H)+.

Provenance & Evidence