Hydrochloric Acid → HCID 45141331, compound

Participants

Reaction Conditions

Reaction Steps

The amine 8 (1.90 g, 7.45 mmol) and oxime ether 13b (0.90 g, 3.44 mmol) were mixed with concentrated hydrochloric acid (15 mL) and the mixture was stirred at 100° C. for 18 h. The reaction mixture was then cooled and washed with ether (3×20 mL). It was then brought to basic pH with NH4OH. The mixture was extracted with chloroform (40 mL×3), and the solution was washed with brine (50 mL), dried (Na2SO4) and concentrated. The residue was dissolved in chloroform (40 mL) and filtered. Hydrochloric acid (2 M HCl in ether, 5 mL) was added to the filtrate. The precipitate that formed was recrystallized from methanol to provide a yellow solid. The solid was dissolved in water, basified with NH4OH and extracted with chloroform. The organic layer was concentrated to dryness. The residue was purified by preparative flash chromatography (SiO2, methanol-chloroform-TEA=3:97:2) to yield the final pure product 14b as a light yellow solid (84.9 mg, 6.1%): mp 210° C. (dec). IR (KBr) 2958, 1449, 1406, 1326, 1246 cm−1; 1H NMR (300 MHz, CDCl3) δ 8.94 (s, 1H), 7.44 (s, 1H), 7.16 (s, 1H), 7.01 (s, 1H), 6.04 (s, 2H), 4.07 (s, 3H), 4.02 (s, 3H), 3.85 (s, 2H), 3.79 (s, 2H), 2.67 (broad s, 4H), 1.82 (broad s, 4H); low resolution ESIMS m/z (rel intensity) 405 (MH+, 15), 334 (100). Anal. (C24H24N2O4.1.75H2O) C, H, N.

Provenance & Evidence