Methacryloyl chloride → N-(5-Hydroxynaphthalen-1-yl)-2-methylprop-2-enamide

Participants

Reaction Conditions

Reaction Steps

227 g of 5-amino-α-naphthol, 1 g of hydroquinone monomethyl ether and 2 litres of pyridine were mixed and cooled to -10° C. by using a freezing medium, and then 110 g of methacrylic acid chloride was added dropwise to the mixture with stirring. After said dropwise addition ended, the solution was stirred at 0°-3° C. for 2 hours, followed by additional 2-hour stirring at 25° C. The reaction solution was poured into 20 litres of ice water. The resultantly formed precipitate was filtered, washed with water and dried. The resulting solids were added into 2 litres of a methanol aqueous 5% sodium carbonate (1/1) mixed solvent, and stirred at 40° C. for 30 minutes and the solution was poured into 4 litres of 5% hydrochloric acid. A large amount of precipitate was formed. This precipitate was suction filtered and recrystallized from ethanol to give 210 g of N-(5-hydroxy-α-naphthyl)methacrylamide having a melting point of 223°-224° C.

Provenance & Evidence