Dimethylformamide → 2-[3-(Pyridin-3-yl)propyl]-1H-isoindole-1,3(2H)-dione

Participants

Reaction Steps

To 7.9 g (28 mmoles) of 3-(3-pyridyl)-1-bromopropane HBr was added 150 mL of dimethylformamide and 27.0 g (145 moles) of potassium phthalimide. The reaction mixture was heated under reflux for 3 hours. The mixture was cooled, diluted with water, and made basic with aqueous potassium hydroxide. The product was then extracted with ethyl acetate, and the extracts were washed with saturated solutions of sodium bicarbonate and sodium chloride, dried and evaporated to give 11.0 g of 2-[3-(3-pyridinyl)propyl]-1H-isoindole-1,3(2H)-dione, m.p. 88°-90°; NMR (CDCl3) δ8.36-8.50 (m, 2H); 7.75-7.90 (m, 2H); 7.57-7.75 (m, 2H); 7.47-7.56 (d, 1H); 7.13-7.32 (m, 1H); 3.63-3.29 (t, 2H); 2.53-2.71 (t, 2H); 1.94-2.10 (m, 2H) .

Provenance & Evidence