Oxalyl chloride → HCID 19422059, compound

Participants

Reaction Steps

6-Oxo-6-(4-methoxyphenylamino)hexanoic acid (509 mg), tetrahydrofuran (12 mL) and dimethylformamide (0.1 mL) were cooled to 0°-5° C. Oxalyl chloride (0.23 mL) was added and the reaction was allowed to stir for fifteen minutes before the addition of N,O-dimethylhydroxylamine hydrochloride (221 mg). After twenty minutes, pyridine (0.8 mL) was added and reaction was warmed to 20°-25° C. Saturated sodium bicarbonate solution (100 mL) was added and the reaction was extracted with dichloromethane (2×30 mL). The combined organic extracts were dried (Na2SO4) and concentrated in vacuo to afford a brown oil which was purified by chromatography eluting with 95:5 ethyl acetate:hexanes. The resulting white solid was recrystallized from ethyl acetate:hexanes to give the title compound as white crystals (133 mg).

Provenance & Evidence