N,N-Diethyl-p-phenylenediamine → N-(4-(Diethylamino)phenyl)-8-methoxy-2-methyl-1,2,3,4-tetrahydronaphthalene-2-carboxamide

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Reaction Steps

The ester from Example 2A (170 mg, 0.73 mmol) was dissolved in THF (2.0 mL) and a solution (3.0 mL) of N,N-Diethyl-benzene-1,4-diamine (332 mg, 2 mmol) and EtMgBr (2.0 mmol) in THF was added at 0° C. The reaction mixture was quenched with aqueous NH4Cl after 3 hours. The mixture was extracted with ethyl acetate (3×15 mL) and the combined extracts were dried over MgSO4 and purified by column chromatography to provide the titled compound (30 mg, 8%). 1H NMR (400 MHz, DMSO-D6) δ 9.03 (s, 1H), 7.33 (d, J=9.2 Hz, 2H), 7.03 (t, J=8.0 Hz, 1H), 6.72 (d, J=7.6 Hz, 1H), 6.73 (d, J=8.0 Hz, 1H), 6.58 (d, J=9.2 Hz, 2H), 3.77 (s, 3H), 3.27 (q, J=7.2 Hz, 4H), 3.11 (d, J=17.2 Hz, 1H), 2.74 (t, J=6.4 Hz, 2H), 2.43 (d, J=17.2 Hz, 2H), 2.15 (ddd, J=6.4, 6.4, 13.2 Hz, 1H), 1.73 (ddd, J=7.2, 7.2, 13.6 Hz, 1H), 1.26 (s, 3H), and 1.04 (t, J=7.2 Hz, 6H). MS (ESI) positive ion 367 (M+H)+; negative ion 365 (M−H)−.

Provenance & Evidence