Transformations of 2-Ethyl-2-methyl-2,3-dihydro-1H-indole at the 3-Position

The oxidation of N-acetyl-2-ethyl-2-methyl-2,3-dihydro-1H-indole with pyridinium chlorochromate, CrO3 · 2 Py, or CrO3 gave N-acetyl-2-ethyl-2-methyl-2,3-dihydro-1H-indol-3-one which was hydrolyzed to 2-ethyl-2-methyl-2,3-dihydro-1H-indol-3-one. The latter was reduced with sodium tetrahydridoborate in ethanol to 3-hydroxy derivative and converted to the corresponding oxime by treatment with hydroxylamine hydrochloride in methanol. Baeyer—Villiger oxidation of 2-ethyl-2-methyl-2,3-dihydro-1H-indol-3-one and Beckmann rearrangement of its oxime were studied.