Naphthalic anhydride → N-Hydroxynaphthalimide

HRID 6613

Reaction equation

Cl.[NH2:2][OH:3].[C:4]12[C:17](=[O:18])O[C:14](=[O:15])[C:12]3=[C:13]1[C:8](=[CH:9][CH:10]=[CH:11]3)[CH:7]=[CH:6][CH:5]=2>N1C=CC=CC=1>[CH:6]1[CH:5]=[C:4]2[C:17]([N:2]([OH:3])[C:14]([C:12]3=[CH:11][CH:10]=[CH:9][C:8](=[C:13]23)[CH:7]=1)=[O:15])=[O:18]

Participants

Conditions

Temperature: 40 °C

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.

Workup

customA 3-L flask equipped with a stirrer
temperaturecooling tube
customthermometer was purged by nitrogen gas
dissolutionto dissolve at room temperature under nitrogen atmosphere
temperaturesubsequently was heated at 70° C. for 1 hour
stirringAfter stirring at 90° C. for 1 hour
temperaturethe reaction mixture was cooled to room temperature
stirringwith stirring
filtrationThe resulting crystalline solid was filtered off
washwashed with 5% by weight of acetic acid aqueous solution
customdried at 80° C. for 20 hours under a reduced pressure

Sources & evidence

ORD record: ord-809c0d72a74341ac83c5e978963cd374
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07084090B2

Linked notes

Loading…