| Wieland-Gumlich aldehyde | |
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| Identifiers | |
| Jmol-3D images | Image 1 Image 2 |
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| Properties | |
| Molecular formula | C19H22N2O2 |
| Molar mass | 310.39 g mol−1 |
| Exact mass | 310.168127958 g mol-1 |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
| Infobox references | |
The Wieland-Gumlich aldehyde is an indoline derived from strychnine. This compound is of some commercial interest as a chemical intermediate. It was first synthesized in 1932 by Wieland and Gumlich in 4 steps from strychnine (1).[1] This degradation study was part of an attempt to elucidate the chemical structure of strychnine.
This degradation takes place through formation of oxime 2 using amyl nitrite, carbamic acid 3 through a Beckmann fragmentation using (thionyl chloride), through a decarboxylation to nitrile 4 and through a nucleophilic displacement with barium hydroxide to alcohol 5. Its hemiacetal gives the Wieland-Gumlich aldehyde (6).
The Wieland-Gumlich aldehyde reverts back to strychnine in a single reaction using malonic acid, acetic anhydride and sodium acetate in acetic acid.[2]
The Wieland-Gumlich aldehyde has been used in the industrial synthesis of alcuronium chloride via dimerization.[3]