Triethylamine → 3,4-Dihydro-N-2-pyridinyl-2-(1H)-isoquinolinamine

Participants

Reaction Steps

Triethylamine (10.0 ml) was added to a solution of 1-bromomethyl-2-(2-bromoethyl)benzene (10 g) and 2-hydrazinopyridine (3.9 g) in dimethylformamide (250 ml), and the mixture was stirred, under nitrogen, at ambient temperature for about 20 mins. The reaction mixture was diluted with water and ethyl acetate. The organic layer was separated, washed with water and brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was triturated with ethyl acetate to afford 5.3 g (65%) of product. Recrystallization of the product from ethyl acetate gave the analytical sample, mp 116-117° C.

Provenance & Evidence