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Finally! Something was made what is a critical compound during the production of a quite special amino acid.
The fun part with this was, that I tried nearly 20 methods to obtain this compound, and all of them failed. At last I tried a Chinese recipe what said that the product will be something that could be easily converted to my molecule, but instead of that compound I got the compound what I need out from the reaction. Better news: 90% isolated yield!
Just a separating funnel with a slightly colored upper, organic layer. It contained an alkaloid derivative what was made from cinchonine. The coloration resulted from a decomposition what was caused by harsh reaction conditions. Interesting is, that only 0,05% of my compound decomposed to give this colored compound, but even in this low concentration it had an intense color as seen.
Cinchonine is an alkaloid found in Cinchona officinalis. It is used in asymmetric synthesis in organic chemistry. It is a stereoisomer and pseudo-enantiomer of cinchonidine what is similar to quinine what was isolated from the cinchona tree and found in Tonic water.
Cinchona alkaloids:
Organic chemistry how I would like to see it.
It was not my reaction, but the person who did it was quite happy, because the side product of his reaction was dissolved in the upper water phase and had a purple color, while his product dissolved in the bottom organic layer and was quite pure.
And what everyone will complain about: who is on the pics is not wearing gloves, since the lab where he works just ran out of nitrile gloves and luckily the product of the reaction and everything what was inside the flask is not more toxic than a chocolate bar.
Unknown reaction product no. 6412686.
It's probably a N-benzyl substituted derivative of the recently produced red dye, but this is note sure, since someone broke the breaker what I used to store the upper organic phase before doing some analytics from it. Besides these, the picture still looks great, it's part of my portfolio!
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A highly fluorescent compound in the upper, etheral, organic layer.
If often use this simple method to know that is there the desired compound in the layer what I will keep and use in the next step or not. The disadvantage of this method is, that things usually do not fluorescence under UV light, so I need at least a well substituted aromatic ring in my molecule to do this.
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If something is worth to publish in the scientific literature, than this is it. A compound what could be polymerized by gentle oxidation to give conductive nano wires what has an insulating layer on them. Pretty interesting and really-really new.
This compound is dissolved in the bottom organic, dichloromethane layer.
The ideal separation: dissolve your compound in an organic solvent, e.g.: ether, wash it with water what will get out everything from it, what is not needed, separate them, remove the solvent in vacuum and be happy with the pure products.
In this case a polyaromatic compound was made is in the upper layer and the copper-amine complex what was used as an oxidizer is in the blue aqueous layer.
Removing fluorescein from the organic phase. During the reaction an amide of fluorescein was made what doesn't have a color and it does not fluoresces under these conditions. So hopefully, the transparency of the upper layer means something good.
The bottom layer is a dilute (1M) sodium hydroxide solution what reacts with the fluorescein to form the highly fluorescent fluoriescein sodium salt what produces this intense green color in the aqueous phase.
Interesting fact: the acid form of the fluorescein does not emit the characteristic intense green color under UV light, it only emits a yellowish-orange color in high concentrations.
