preparation | 2- [(6-bromopyridin-2-yl) methyl] -2, 3-dihydro-1h-isoindole-1, 3-dione (2.5g,7.88mmol,1.0 equiv) in absolute ethanol (78ml), A 250ml round bottom flask equipped with a magnetic stir bar and condenser was loaded and heated to reflux until complete dissolution (approximately 15 minutes). To the homogeneous solution was added hydrazine monohydrate (1.58g,1.53mL,31.53mmol,4.0 equiv). Within one minute, the reaction mixture turned yellow. The reaction mixture was heated for 3 hours during which time the mixture solidified into a thick white suspension. Another 50ml of ethanol was added and the mixture was stirred for an additional 2 hours. The reaction was cooled to room temperature and then to 0 °c to precipitate the hydrazine/phthalimide adduct that disintegrated in solution. The precipitate was filtered on Buchner. The precipitate was thoroughly washed with absolute ethanol, and the filtrate was partially concentrated. There was still some solids in the suspension, which was then filtered with cold EtOH. The filtrate was concentrated to dryness to give a solid. |