Sulfuric Acid → Hydrocotarnine

Participants

Reaction Steps

0.27 g (1.02 mmol) of 4-ethoxy-8-methoxy-2-methyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline (8) was dissolved in 15 ml of acetic acid, and the solution was added with 200 mg of 5% palladium carbon and 0.1 ml of 97% sulfuric acid and hydrogenated at 75° C. for 1 hour and 40 minutes. After cooling, the catalyst was filtered off and the filtrate was added with a small quantity of an aqueous solution of sodium hydroxide and concentrated under reduced pressure. The residue was added with 10 ml of water and made basic with an aqueous solution of sodium hydroxide. The resulted solution was extracted twice with 5 ml of methylene chloride and the extract was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to obtain 0.20 g of 8-methoxy-2-methyl-6,7-methylenedioxy-1,2,3,4-tetrahydroisoquinoline (13) as a crystal. Yield: 89%.

Provenance & Evidence