Triethylamine → N-[4-methoxy-3-(naphthylmethoxy)phenyl]naphthylformamide

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Reaction Steps

N-[4-methoxy-3-(naphthylmethoxy)phenyl]naphthylformamide (Exemplary Compound 47) was prepared using the same experimental conditions used to prepare Exemplary Compound 52 (Scheme X, above). From 4-methoxy-3-(2-naphthylethoxy)phenylamine (350 mg, 1.25 mmol) and 1-naphthoyl chloride (240 mg, 1.25 mmol) in 10 mL of dimethyl acetamide containing triethylamine (1 mL, 7.17 mmol) stirred at room temperature for 16 h., was obtained 280 mg of product in (52%) yield as white needles after recrystallization from ethyl acetate/hexane: mp 161-163° C. 1H NMR (400 MHz, Me2SO-d6) δ3.74 (s, 3H); 5.52 (s, 2H); 7.01 (d, 1H, J=8.8); 7.43 (dd, 1H, J=2.3, 8.7); 7.51-7.74 (m, 9H); 7.94-8.21 (m, 6H); 10.43 (s, 1H). Anal. Calcd for C29H23NO3: C, 80.35; H, 5.35; N, 3.23. Found: C, 80.25; H, 5.39; N, 3.19.

Provenance & Evidence