HCID 9888691, compound → HCID 135744186, compound

Participants

Reaction Steps

9-Benzyloxy-2,3,8-trimethoxydibenzo[c,h]cinnoline, 42, (5 mg, 0.012 mmol) was hydrogenated overnight in ethyl acetate (25 mL) at 26 lb./sq. in. using 10% palladium on carbon (1.5 mg). The solution was passed through a Celite bed and the catalyst was washed with ethyl acetate (10 mL×3). Concentration of the ethyl acetate solution in vacuo gave the crude product. Chromatography using a 50:45:5 mixture of hexanes:ethyl acetate:methanol as eluting solvent gave compound 34 (3 mg) in 76% yield; 1H NMR (DMSO-d6) δ4.00 (3H, s), 4.10 (3H, s), 4.12 (3H, s), 7.66 (1H, s), 8.02 (2H, s), 8.21 (1H, d, J=8.4), 8.38 (1H, d, J=8.9), 8.96 (1H, s); 13C NMR δ55.9, 56.4, 103.1, 103.8, 108.5, 109.1, 117.4, 117.8, 118.0, 125.7, 128.1, 131.3, 140.4, 143.8, 150.5, 150.7, 151.3, 152.4; HRMS (EI) calcd for C19H16N2O4 m/z 336.111; found: 336.1109.

Provenance & Evidence