反应详情

N-Hydroxyphthalimide (3.30 g, 20.2 mmol) was dissolved in NMP (50 ml) and 4-cyanobenzyl bromide (4.35 g, 22.2 mmol) was added followed by drop-wise addition of 1,8-diazabicyclo[5,4,0]-undec-7-ene (DBU) (3.0 ml, 20.1 mmol). After complete addition of DBU (ca. 15 min.) the reaction mixture was stirred at room temperature for 65 min. The mixture was poured into ice cooled 1M aqueous hydrochloric acid (500 ml) and the precipitated material was collected by filtration and washed with water and dried under high vacuum. This phthalimide derivative (5.31 g, 19.1 mmol) was suspended in ethanol (40 ml) and a solution of hydrazine monohydrate (0.93 ml, 19.1 mmol) in ethanol (10 ml) was added drop wise. The reaction mixture was heated to reflux and stirred for 2.5 hours. The mixture was cooled to room temperature and the solid material removed by filtration and washed with ethanol. The combined filtrates were evaporated under reduced pressure. The residue was resuspended in EtOAc and the undissolved material was removed by filtration. The EtOAc filtrate washed with saturated aqueous NaHCO3, and water, dried (MgSO4) and evaporated under reduced pressure. The residue was suspended in diethyl ether (150 ml) and concentrated hydrochloric acid (50 ml) was added and the resulting slurry was stirred at room temperature for 30 min. The precipitated product was isolated by filtration, washed with diethyl ether and dried in vacuo, affording the title compound (2.24 g) as a white powder. 1H-NMR (DMSO-d6) δ 11.26 (bs, 3H), 7.90 (d, 2H), 7.63 (d, 2H), 5.17 (s, 2H).

1. additionThe mixture was poured into ice
2. filtrationthe precipitated material was collected by filtration
3. washwashed with water
4. customdried under high vacuum
5. temperatureThe reaction mixture was heated
6. temperatureto reflux
7. stirringstirred for 2.5 hours
8. temperatureThe mixture was cooled to room temperature
9. customthe solid material removed by filtration
10. washwashed with ethanol
11. customThe combined filtrates were evaporated under reduced pressure
12. customthe undissolved material was removed by filtration
13. washThe EtOAc filtrate washed with saturated aqueous NaHCO3, and water
14. dry with materialdried (MgSO4)
15. customevaporated under reduced pressure
16. additionconcentrated hydrochloric acid (50 ml) was added
17. stirringthe resulting slurry was stirred at room temperature for 30 min
18. customThe precipitated product was isolated by filtration
19. washwashed with diethyl ether
20. customdried in vacuo