Aniline → 2-Naphthalenecarboxamide, 3-hydroxy-7-methoxy-N-phenyl-

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Reaction Steps

2-hydroxy-6-methoxy-3-naphthoic acid (10 g, 0.045 moles) and thionyl chloride (6 g, 0.05 moles) are placed inside a 250 ml three-neck flask containing about 100 ml of methylene chloride. The mixture is stirred and brought to reflux under a nitrogen atmosphere. A catalytic amount of dimethylformamide is added. After about 20 minutes, all of the naphthoic acid is reacted and goes into solution. The solution is cooled to room temperature, and transferred to a 250 ml pressure equalizing funnel. The resulting 2-hydroxy-6-methoxy-3-napthoic acid chloride is then added to a 50 ml methylene chloride solution containing 5.6 g of aniline and 8 g of N,N-diethylaniline. The mixture is heated to reflux for about another 3 hours. After being cooled to room temperature, the mixture is filtered and washed with methanol, yielding 9.1 grams of a crude product after vacuum drying. The crude product is then purified by recrystallization from a mixture of dimethylformamide and methanol, affording 7.8 grams of a creamy while solid, 2-hydroxy-6-methoxy-3-naphthanilide (about 59%), having a melting point of 230° C. and an IR(KBr) of about 1640 cm-1 (amide C=O).

Provenance & Evidence