1-Alkoxytryptamines, reaction with aqueous

In the reaction of 1-alkoxytryptamines with aqueous HCl, 5-chlorotryptamines (213), 7-chlorotryptamines (214), and dealkoxylated tryptamines (53) are produced, and the results are summarized in Table V. Interestingly, the 1-substituent is an important factor in governing the yield of 5-chlorotryptamines (213). As the substituent changes in turn from hydroxy to methoxy, l-(2-methoxycarbonyl)ethoxy, and l-(2-methoxycarbonyl-l-methyl)ethoxy groups (entries 1—4), the yield of 213a increases dramatically. 

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