Synthesis of dl-Esermethole.

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Abstract
N-Methyl-α-bromo-γ-phthalimidobutyranilide (X) was treated with fused aluminum chloride according to the method of Stolle, giving the corresponding oxindole derivative (XI), from which the phthalimido group was removed smoothly by Ing's method. When the amine (XII) thus prepared was treated with metallic sodium 1-methyltryptamine was produced in a fair yield as the sole isolable product and the expected cyclized product, dl-nordesoxyeseroline (A), once supposed as folicanthine, was not traced in the reduction product. However, when 1, 3-dimethyl-3-(β-methylaminoethyl) oxindole (VIII), prepared in a silmilar manner as (XI), was subjected to the same reduction, there was obtained dl-esermethole (IX), which had already been prepared by Preobrazhenskii, et al. a few years ago by a different method. The presence or absence of a hydrogen atom at 3-position of oxindole derivatives was thus shown to be a decisive factor for the course of their reduction.

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