Ammonium Hydroxide → HCID 45141333, compound

Participants

Reaction Conditions

Reaction Steps

The amine 8 (560.3 mg, 2.19 mmol) and oxime ether 13d (320.2 mg, 1.10 mmol) were mixed together with concentrated hydrochloric acid (10 mL) and the mixture was stirred at 100° C. for 3 h. The reaction mixture was then cooled and washed with ether (3×20 mL). It was then brought to basic pH with 28% aqueous NH4OH. The mixture was extracted with CHCl3 (3×40 mL), and the organic layer was washed with brine (50 mL), dried with anhydrous Na2SO4 and concentrated. The residue was diluted in CHCl3 (40 mL) and filtered. Hydrochloric acid (2 M HCl in ether, 10 mL) was added to the filtrate. A dark yellow precipitate was obtained and recrystallized from methanol to provide a bright yellow solid. NH4OH (2 mL) was added to the yellow solid and the mixture was concentrated to dryness. The residue was purified by preparative flash chromatography (SiO2, methanol-chloroform-TEA=10:90:2) to yield the final pure product 14d as a yellow solid (16.7 mg, 3.5%): mp 296° C. (dec). IR 3400, 1489, 1455, 1245, 1159 cm−1; 1H NMR (300 MHz, CDCl3) δ 8.98 (s, 1H), 7.47 (s, 1H), 7.24 (s, 1H), 7.08 (s, 1H), 6.04 (s, 2H), 4.11 (s, 3H), 4.04 (s, 3H), 3.91 (s, 2H), 3.68 (s, 2H), 2.65 (brs, 4H), 2.56 (brs, 4H), 2.34 (s, 3H); ESIMS m/z (rel intensity) 434 (MH+, 100), 334 (25). Anal. (C25H27N3O4.3.5H2O) C, H, N.

Provenance & Evidence