Abstract
α-Bromo-α-methyl-δ-phthalimidovaler-p-anisidide (VIII) was fused with aluminum chloride according to Stolle to give 5-methoxy-1, 3-dimethyl-3-(γ-phthalimidopropyl) oxindole (IX) after methylation. Phthalimido group could be readily removed from this compound by the standard method, furnishing 3-(γ-aminopropyl) oxindole derivative (X), which was then monomethylated to (XI). This compound could also be prepared advantageously by reducing 5-methoxy-1, 3-dimethyl-3-(β-cyanoethyl) oxindole (XII) catalytically in the presence of methylamine. On being reduced with sodium in boiling ethanol the latter gave rise to a single dl-homoesermethole (III) in a fair yield, no isomeric base being detected in the reduction product.
