Acetic Anhydride → HCID 20337291, compound

Participants

Reaction Steps

A solution of 8.6 g (20 mm) of 3-acetyl-7,8-diacetoxy-1-phenyl-6-methylthio-2,3,4,5-tetrahydro-1H-3-benzazepine (prepared by reacting the dihydroxy parent with an excess of acetic anhydride in pyridine at room temperature) in 40 ml of methanol at -5° is treated with 40 ml of 0.52 M sodium periodate (20.8 mm) dropwise over 15 minutes at 0°. The mixture is cooled overnight, then filtered to give a solid which is washed with methylene chloride. The organic extracts are combined, dried and evaporated in vacuo. The residue is heated at reflux in ethanolic hydrochloric acid overnight. The volatiles are removed and the residue taken up in water. Neutralization with ammonia and extraction with ethyl acetate gives the desired 7,8-dihydroxy-6-methylsulfinyl-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine. The hydrochloride salt is formed by treatment with ethereal hydrogen chloride.

Provenance & Evidence