Abstract
AbstractReaction of N‐methylaniline with 40% glyoxal yields 1‐methyl‐2‐(N‐methyl‐N‐phenylglycyl)‐3‐(N‐methylanilino)indole (1a) as the main product together with 1‐methyl‐3‐(N‐methylanilino)indole (1b). The reaction appears to be general for aromatic secondary amines since N‐ethylaniline and N‐phenylbenzylamine yield the corresponding indoles. The structure of 1a has been verified by single crystal X‐ray diffraction. Compound 1a (C25H25N3O) crystallized in the triclinic space group Pl̄ with cell dimensions a = 10.085(3)Å, b = 10.371(3)Å, c = 11.908(5)Å, α = 74.2(3)°, β = 74.7(3)° and γ = 60.7(2)° with Z = 2. The complete 1H and 13C nmr assignment of indoles 1a and 1b was achieved from two‐dimensional HETCOR and COSY spectra with the aid of homonuclear and heteronuclear double resonance experiments.
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