Hydrochloric Acid → HCID 22716427, compound

Participants

Reaction Steps

6-(2-Amino-5-methoxyphenyl)-2,3-dimethoxynaphthalene (33) (60 mg, 0.20 mmol) was dissolved in acetic acid (1.5 mL) and concentrated hydrochloric acid (0.3 mL). The solution was cooled in an ice bath and diazotized by dropwise addition of a solution of sodium nitrite (0.12 g in 1.2 mL water). The resulting diazonium solution was allowed to rise to room temperature slowly and left overnight. To the resulting red solution with some precipitate, 50 mL water was added and then extracted with ethyl acetate (40 mL×3). The organic layers were combined and washed with diluted sodium hydroxide solution first, then with water and brine. Dried with anhydrous sodium sulfate and evaporated in vacuo. The crude product was purified by column chromatography on silica gel using 35:65 hexanes:ethyl acetate to give the pure 5 (16 mg) in 26% yield; mp 215-217° C.; IR (KBr) 2987, 1617, 1504, 1486, 1394, 1277, 1231, 1167 cm−1; UV (MeOH) 288, 262, 232 nm (log ε=4.71, 4.66, 4.58); 1H NMR (CDCl3) δ4.07 (3H, s), 4.09 (3H, s), 4.22 (1H, s), 7.29 (1H, s), 7.46 (1H, dd, J1=9.1, J2=2.6), 7.72 (1H, J=2.5), 7.99 (1H, d, J=8.9), 8.20 (1H, d, J=9.0), 8.60 (1H, d, J=9.1), 9.17 (1H, s); 13C NMR δ56.31, 56.51, 56.90, 100.27, 104.61, 107.73, 117.00, 118.66, 121.31, 124.25, 126.98, 129.09, 131.40, 133.34, 141.76, 143.70, 151.23, 151.31, 161.95; HRMS (EI) calcd for C19H16N2O3 m/z: 320.1161; found: 320.1144.

Provenance & Evidence