The photolysis of enamine N-metho salts

✍ Scribed by Tai-Teh Wu; Jerome L. Moniot; Maurice Shamma

• Book ID: 104212230
• Publisher: Elsevier Science
• Year: 1978
• Tongue: French
• Weight: 189 KB
• Volume: 19
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)70535-1

✦ Synopsis

As part of a systematic study of the photolysis of enamines within the framework of protoberberine chemistry, we had occassion to subject a methanolic solution of the known N-methyl dihydroberberine salt 1 1' to sunlight for one hour. The product, Isolated in 27% yield, proved to be the crystalline 1-(2~methyl-3~~dlmethoxybenzoyl~-6,7-methylenedioxy-3,4-dihydroisoqulnoline (21, CZ,,HIPNCI,, mp 107-llO" (EtOH), bzE$' 1660 cm -1 , while the starting material 1 could be recovered in 55% yield. For the purpose of characterization, the imino ketone 2 was reduced with sodium borohydride to the amino alcohol 3, C,,HZ3N~, mp 101-103° (CHC13-acetone).