Reaction #6709

Reaction equation

hydroxylamine-hydrochloride

1,8-naphthalenedicarboxylic anhydride

→

N-hydroxynaphthalimide

Yield 81.0%

Solvents

pyridine

Conditions

Workup

1. 1
   OtherA 3-L flask equipped with a stirrer
2. 2
   Temperaturecooling tube
3. 3
   Otherthermometer was purged by nitrogen gas
4. 4
   workup.DISSOLUTIONto dissolve at room temperature under nitrogen atmosphere
5. 5
   Temperaturesubsequently was heated at 70° C. for 1 hour
6. 6
   workup.STIRRINGAfter stirring at 90° C. for 1 hour
7. 7
   Temperaturethe reaction mixture was cooled to room temperature
8. 8
   workup.STIRRINGwith stirring
9. 9
   FiltrationThe resulting crystalline solid was filtered off
10. 10
    Washwashed with 5% by weight of acetic acid aqueous solution
11. 11
    Otherdried at 80° C. for 20 hours under a reduced pressure

Procedure

A 3-L flask equipped with a stirrer, cooling tube and thermometer was purged by nitrogen gas. 55.2 g (770 mmol) of hydroxylamine-hydrochloride (purity of 97%) and 1.2 L of pyridine were added to the flask and were stirred to dissolve at room temperature under nitrogen atmosphere. To the stirred mixture, 138.7 g (700 mmol) of 1,8-naphthalenedicarboxylic anhydride was added. The stirred mixture was heated at 40° C. for 1 hour and subsequently was heated at 70° C. for 1 hour. After stirring at 90° C. for 1 hour, the reaction mixture was cooled to room temperature with stirring. The resulting crystalline solid was filtered off and washed with 5% by weight of acetic acid aqueous solution and dried at 80° C. for 20 hours under a reduced pressure to yield 120.7 g (81%) of N-hydroxynaphthalimide with yellow color.

Source