Phthalic Anhydride → N-Allylphthalimide

A 500 mL round-bottom flask was charged with phthalic anhydride (22.2 g, 150 mmol) and anhydrous DMF (150 mL) and stirred at room temperature for 5 min to dissolve the phthalic anhydride. To the solution was slowly added allylamine (11.26 mL, 150 mmol) followed by 20 g of 3A molecular sieves. The resulting mixture was stirred at room temperature 10 minutes and then heated under nitrogen at 80° C. for 16 hrs. The reaction mixture was cooled to room temperature and filtered. To the mother liquor was added 300 mL of EtOAc and 300 mL of brine solution. The organic layer was separated, washed twice with 300 mL of water, and dried over MgSO4. The drying agent was removed by filtration and the mother liquor concentrated. The resulting solid was recrystalized from CH2Cl2/hexane to yield 27.75 g (98% yield) of N-allylphthalimide (1-1).

1. stirringThe resulting mixture was stirred at room temperature 10 minutes
2. temperatureheated under nitrogen at 80° C. for 16 hrs
3. temperatureThe reaction mixture was cooled to room temperature
4. filtrationfiltered
5. additionTo the mother liquor was added 300 mL of EtOAc and 300 mL of brine solution
6. customThe organic layer was separated
7. washwashed twice with 300 mL of water
8. dry with materialdried over MgSO4
9. customThe drying agent was removed by filtration
10. concentrationthe mother liquor concentrated
11. customThe resulting solid was recrystalized from CH2Cl2/hexane

ORD record

ord-88a93c6d3add4bd5939276fb098166ba

Source dataset

uspto-grants-2001_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06262268B1