HCID 22716445, compound → HCID 22716433, compound

Participants

Reaction Steps

6-(4-Methoxy-2-nitrophenyl)-2,3-dimethoxynaphthalene 29 (18 mg, 0.053 mmol) was hydrogenated overnight in ethyl acetate (20 mL) at 40˜45 lb./sq. in. using 10% palladium on carbon (10 mg) as catalyst. The reaction solution was passed through a Celite bed and the catalyst was washed with ethyl acetate (10 mL×3). Concentration in vacuo gave the crude product. The residue was chromatographed using a 60:40 mixture of hexanes:ethyl acetate to give 32 (14 mg) in 85% yield; 1H NMR (CDCl3) δ3.83 (3H, s), 4.01 (3H, s), 4.03 (3H, s), 6.37 (1H, d, J=2.5), 6.45 (1H, dd, J1=8.3, J2=2.4), 7.12-7.16 (3H, m), 7.42 (1H, dd, J1=8.4, J2=1.7), 7.72-7.77 (2H, m); 13C NMR δ55.72, 56.40, 101.56, 104.79, 106.59, 106.78, 121.49, 126.36, 126.81, 127.24, 128.47, 129.89, 131.98, 135.55, 145.28, 150.01, 150.25, 160.49; HRMS (EI) calcd for C19H19NO3 m/z: 309.1365; found: 309.1355.

Provenance & Evidence