Various Syntheses of Tryptamines

[Rhodium]

Studies in. the Indole Series. Part I. Indolylalkylamines
B. Heath-Brown and P. G. Philpott

J. Chem. Soc. 7165-7178 (1965)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/tryptamine.synthesis-1.pdf)

Abstract
The preparation of a large series of indolylalkylamines is described, including ?-alkyl-, ?,?-dialkyl-, and N-alkyltryptamines. New methods include a modification of the Abramovitch synthesis giving ?,N-dimethyltryptamines directly.
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Studies in the Indole Series. Part II. Indolylalkylhydroxylamines
A. Cohen and B. Heath-Brown

J. Chem. Soc. 7179-7184 (1965)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/tryptamine.synthesis-2.pdf)

Abstract
A series of indolylalkylhydroxylamines (II) has been prepared by suitable reduction of nitroalkylindoles. Some cases of hydrogenation of such nitro-compounds are discussed, in which the indole nucleus is reduced with retention of the nitro-group.
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Studies in the Indole Series. Part III. The Japp–Klingemann Reaction
B. Heath-Brown and P. G. Philpott

J. Chem. Soc. 7185-7193 (1965)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/tryptamine.synthesis-3.pdf)

Abstract
A number of indoles have been prepared by the Fischer cyclisation method. The intermediate hydrazones were made by the Japp–Klingemann reaction, in the course of which several new azo-esters were obtained. These little-known compounds are characterised by analysis and by infrared and ultraviolet spectra.

[Rhodium]

The Melting Point and Structure of Tryptamine
A. H. Jackson and A. E. Smith

J. Chem. Soc. 3498-3500 (1965)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/tryptamine.mp-structure.pdf)
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The Synthesis of 3-?-Aminoethylindole
Arthur James Ewins

J. Chem. Soc. 99, 270-273 (1911)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/tryptamine.ewins.pdf)
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A New Synthesis of Indoles Particularly Suitable for the Synthesis of Tryptamines and Tryptamine Itself
Ian Fleming and Michael Woolias

J. Chem. Soc. Perkin Trans. 1, 829-837 (1979)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/tryptamine.synthesis.pdf)

Abstract
2-Amino-1-o-bromophenylethanols (4) give indoles (5) when heated to 140-170°C in a solution of ammonia in methanol. The reaction is suitable for the synthesis of a wide variety of 1-, 3-, 5-, and 6-substituted indoles and, because the starting materials are easy to make, it is particularly suitable for the synthesis of N,N-disubstituted tryptamines (15). Tryptamine itself can be made in 31% yield (based on o-bromobenzoic acid) by using benzyl groups as the N-substituents, and removing them by hydrogenolysis.