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Paper | Special issue | Vol 47, No. 1, 1998, pp.367-373
Published online, 1st January, 1970
DOI: 10.3987/COM-97-S(N)32
Synthesis of 4-(2-Aminoethyl)indoles through Claisen ortho-Amide Rearrangement of3-Hydroxy-2-methoxyindolines

Tomomi Kawasaki, Hiroaki Ohtsuka, Ado Mihira, and Masanori Sakamoto*

*Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan


Reaction of 3-hydroxy-2-methoxyindolines (5) with amide acetal (6) and ketene aminal (13) gives 4carbamoylmethylindole (9) and -indoline (11), which are converted into 4-(2-aminoethyl)indole (7) by treatment of the indoline (11) with hydrochloride followed by sodium hydroxide to form the indole (9), and then by reduction of 9 with lithium aluminum hydride.