This kind of reaction is called Knoevenagel or Henry condensation, and takes place between ketones/aldehydes and deprotonated nitroalkanes, usually with the aid of a base acting as deprotonating catalyst.
The ammonium acetate acts on the nitroethane as deprotonating catalyst, which then condenses with the aldehyde under dehydration to give the following compound:
![](https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000448477-henryindole2.gif)
Now if you substitute nitro
Ethane with nitro
Methane, you arrive at the following nitrostyrene compound:
![](https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_docs/000448477-henryindole3.gif)
When you reduce the C=C bond and the nitro group (LiAlH
4, or NaBH4 and then hydrogen/Pd/C), you arrive at (alpha-alkylated) tryptamines, nitromethane giving tryptamine, nitroethane AMT, nitropropane will result in two different condensation products of which one will result in AET upon reduction, and so on.
Shulgin prepared almost all his several hundred phenethylamines/amphetamines/tryptamines in the same fashion, the only difference is the starting material: benzaldehydes for phenyl compounds, indole-aldehyde for tryptamines...
Interesting; why do so much bees get grey hair while trying to decarboxylate tryptophan when there is such an easy way to tryptamine? Is it the indole-3-aldehyde (which could be hard to get)?
(hest: if you use MeNO2 and reduce to tryptamine, you can synthesize virtually every N-alkylated tryptamine by reacting the appropriate alkylhalide with tryptamine in aequ. solvent in your microwave, according to this journal I requested recently in "wanted references"...
Aqueous N-alkylation of amines using alkyl halides: direct generation of tertiary amines under microwave irradiation(Yuhong Ju and Rajender S. Varma; Green Chem., 2004, 6 (4), (219-221)) - unfortunately noone seems to have access to the "Green Chem." journal, but this one looks cute, don't you think? From indolealdehyde to DMT with three easy reaction steps (henry/reduction/alkylation), of which two are done in a (modified) domestic microwave - sounds good!
![Cool 8)](https://thevespiary.org/talk/Smileys/default/cool.gif)
- Can't any friendly bee perhaps check if his/her library has this journal? It would match soo good here...
![Roll Eyes ::)](https://thevespiary.org/talk/Smileys/default/rolleyes.gif)
)
indole_amine