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ChemicalBook CAS DataBase List N-Hydroxynaphthalimide triflate
85342-62-7

N-Hydroxynaphthalimide triflate synthesis

2synthesis methods

A mixture of 10.0 g (0.051 mol) naphthalic anhydride, 3.9 g (0.056 mol) hydroxylamine hydrochloride and 80 ml pyridine was taken and stirred at 100 °C for 10 hours. After cooling to room temperature, the reaction solution was poured into 1 N hydrochlor

-

Yield: 97.6%

Reaction Conditions:

Stage #1:N-hydroxy-1,8-naphthalenedicarboximide;trifluoromethane sulfonyl chloride in 5,5-dimethyl-1,3-cyclohexadiene at 10; for 7 h;
Stage #2: with sodium hydroxide in 5,5-dimethyl-1,3-cyclohexadiene;water for 0.5 h;Solvent;Temperature;

Steps:

1-11
In a 1L four-necked flask equipped with a stirring blade, a condenser, and a thermometer, add the solvent 330mL xylene, 100 g of N-hydroxy-1,8-naphthalimide, turn on the stirring, and lower the temperature to the temperature of the reaction system at 10°C. 87 g of trifluoromethanesulfonyl chloride was slowly added dropwise to the reaction system, and the reaction was kept warm for 7 hours. The reaction process was monitored. After sampling and detection, 148g of NaOH solution with a mass concentration of 14% was added dropwise to the system, and the mixture was uniformly stirred for 30 minutes. Extract and separate the phases under the action of the solvent xylene. After standing for separation, the xylene phase is concentrated under reduced pressure at 65-75 °C. The conditions of reduced pressure concentration in this example are at 70°C, and the pressure of reduced pressure concentration is 0.099MPa-0.1MPa, Cool down to room temperature and filter with suction to obtain the crude product of wet N-hydroxynaphthalimide triflate. The solid N-hydroxynaphthalimide trifluoromethanesulfonate obtained by recrystallizing the crude product with 4 times the weight of 20% toluene/80% water (V/V) at 87°C is dried below 80°C to obtain a solid product 158.2g. The product yield was 97.6%.

References:

Hebei Kailiang Biological Technology Co., Ltd.;Zhang Chen;Sun Jiawei;Li Shilei;Du Zhaolei CN112094231, 2020, A Location in patent:Paragraph 0017; 0020-0034

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