Hydrochloric Acid → N-(5-Hydroxynaphthalen-1-yl)-2-methylprop-2-enamide

Participants

Reaction Conditions

Reaction Steps

Into a mixture comprising 227 g of 5-amino-α-naphthol, 1 g of hydroquinone monomethyl ether and 2 liters of pyridine was dropwise added with stirring 110 g of methacrylic acid chloride cooled to -10° C. by the use of a coolant. After completion of the addition, the mixture was stirred at 0°-3° C. for 2 hours, followed by stirring at 25° C. for 2 hours. Thereafter, the reaction liquid was poured into 20 liters of water to form a precipitate which was then filtered, water-washed and then dried to obtain solids. The solids were added to 2 liters of a 1:1 mixture of methanol and a 5% sodium carbonate solution, and after stirring at 40° C. the mixture was poured into 4 liters of a 5% hydrochloric acid to form a large amount of precipitate. The precipitate was filtered by suction and then recrystallized from ethanol to obtain 210 g of N-(5-hydroxy-α-naphthyl)methacrylamide, m.p. 223°-224° C.

Provenance & Evidence