7-(4,5-Methylenedioxy-2-nitrophenyl)-2-methoxynaphthalene → 7-(2-Amino-4,5-methylenedioxyphenyl)-2-methoxynaphthalene

Participants

Reaction Steps

7-(4,5-Methylenedioxy-2-nitrophenyl)-2-methoxynaphthalene 48 (100 mg, 0.31 mmol) was hydrogenated overnight in ethyl acetate (35 mL) at 40˜45 lb./sq. in. using 10% palladium on carbon (30 mg) as catalyst. The reaction solution was passed through a Celite bed and the catalyst was washed with ethyl acetate (10 mL×3). The ethyl acetate solution was concentrated in vacuo gave the crude product. The residue was chromatographed using a 75:25 mixture of hexanes:ethyl acetate to give 49 (75 mg) in 83% yield; IR (KBr) 3426, 3366, 2364, 2339, 1629, 1503, 1487, 1467, 1233, 1215, 1187 cm−1; 1H NMR (CDCl3) δ3.64 (2H, s), 3.94 (3H, s), 5.92 (2H, s), 6.40 (1H, s), 6.76 (1H, s), 7.15-7.20 (2H, m), 7.40 (1H, dd, J1=8.3, J2=1.7), 7.75-7.85 (3H, m); 13C NMR δ55.83, 98.35, 101.27, 106.25, 110.65, 119.35, 120.29, 125.82, 127.35, 128.31, 128.72, 129.67, 135.34, 137.99, 138.99, 141.17, 148.16, 158.49; HRMS (EI) calcd for C18H15NO3 m/z: 293.1052; found: 293.1052.

Provenance & Evidence