Sulfuric Acid → HCID 58424883, compound

Participants

Reaction Steps

The compound (27 mg, 0.069 mmol) prepared in step 3 was dissolved in methanol (5 ml) and dichloromethane (5 ml), and added with 10%-palladium. The mixture was stirred for 18 hours at room temperature under hydrogen gas. Once the reaction was completed, 10%-palladium (Pd) was removed by celite filter and the filtrate was concentrated under reduced pressure. The residue was dissolved in trifluoroacetic acid (TFA, 2 ml), and the resultant mixture was added with anisol (0.64 ml, 0.58 mmol) and 12 N sulfuric acid aqueous solution (0.097 ml, 1.17 mmol). The reaction mixture was stirred for 18 hours at 100° C. The mixture was stirred for one hour at 140° C. The mixture was poured into a cold sodium bicarbonate aqueous solution and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by flash column chromatography (dichloromethane:methanol=7:1) to obtain the title compound (7.5 mg, yield: 47%, yellow solid).

Provenance & Evidence