Benzaldehyde from benzoyl chloride, cyanide, and quinoline - the Reissert reaction!

I came to terms with the low yield of this reaction with my quinoline. The ROI of purifying quinoline wasn't worth it after 3 weeks of trial and error with this.
As a side note, I really do want a proper 4 decimal place scale, but something my analytical chemistry professor said several years ago has haunted me and made me not want to buy one on ebay: the conditions involved with shipping such a balance would almost definitely damage whatever it is, something electronic that I don't remember and am unfamiliar with, that gives the balance its ability to measure mass to the desired 0.1mg sensitivity. Maybe more modern balances don't have this issue. If you have some knowledge on this topic, let me know in the comments.
Mechanism explanation:
The Reissert reaction is a type of addition reaction.
Because I had limited space on my chalkboard, I chose not to include counterions, i.e. chloride (Cl-) in the first part of the reaction and bisulfate (HSO4-) in the second part of the reaction. Keep in mind that they're always present, they don't just appear out of nowhere.
The free electron pair of quinoline's nitrogen atom attacks the carbon of the acyl chloride, and one of the bonds from the C=O double bond moves to the oxygen.
The C-Cl bond moves to the Cl to give a free chloride ion, and the negative charge on the oxygen moves to the C-O(-) single bond. This results in an intermediate that can undergo rearrangement between 3 forms. The second form is the most important, and in the next step, a free cyanide ion attacks the positively charged carbon adjacent to the quinoline's nitrogen. The potassium cyanide's potassium combines with the free chloride previously generated and potassium chloride is produced. The heterocyclic nitrogen's free electron pair moves to the adjacent N-C bond, one of the C=O double bonds attacks the nitrile's carbon, and one of the nitrile's triple bonds attacks the hydrogen of a hydronium ion, the O-H bond of which moves to the hydronium's positively charged oxygen atom. A water molecule is produced. The intermediate's C-H bond adjacent to the heterocyclic nitrogen moves to the C-N(+) bond, while one of the bonds from the adjacent C=N(+) attacks the hydrogen of a hydronium ion, the O-H bond of which moves to the hydronium's positively charged oxygen atom. A water molecule is produced. The intermediate's carbon center of the C=N imine is attacked by an electron pair of water's oxygen, and one of the imine's C=N bonds attacks a free proton. The intermediate's O-H bond moves to the adjacent C-O bond, the heterocyclic C-O bond moves to the adjacent C-O bond, and the C-(N+) bond moves to the positively charged nitrogen. An aldehyde is produced, and the amide analog of quinaldic acid is produced.
This amide undergoes further hydrolysis to produce quinaldic acid. All of the amide hydrolysis reaction steps are reversible. One of the amide oxygen's electron pairs attacks the hydrogen of a hydronium ion, the O-H bond of which moves to the hydronium's positively charged oxygen atom. A water molecule is produced. An electron pair of a free water molecule's oxygen attacks the carbon center of the quinaldic acid amide, and one of the bonds from the C=O(+) double bond moves to the positively charged oxygen. An electron pair of a free water molecule's oxygen attacks the hydrogen of the +(OH2), and the same +(OH2)'s O-H bond moves to the positively charged oxygen. A hydronium molecule is produced. The resulting intermediate is odd-looking. The non-heterocyclic nitrogen's free electron pair attacks the hydrogen of a hydronium ion, the O-H bond of which moves to the hydronium's positively charged oxygen atom. A water molecule is produced. The +(NH3) is now a good leaving group, so the C-N bond moves to the positively charged nitrogen of it. One of the free electron pairs of one of the O-H group's oxygens moves to the adjacent C-O bond. The O-H bond of the positively charged oxygen moves to that oxygen, and the free lone electron pair of the ammonia molecule produced in the previous step attacks the hydrogen of the same O-H bond. Quinaldic acid is produced, along with ammonium bisulfate.

[@Cairlos001]

Interesting chemistry and great commentary as well. Looking forward to future videos.

[@philouzlouis2042]

Hi ChemSungeon,
Nice video, and synthesis demonstration.
You of course need to make quinoline; this can be done via Skraup synthesis via aniline (or nitrobenzene and iron and water or acid), via propantriol (glycerine) (and its transcient accrolein from H2SO4 and heat); or any other OTC pathway.
PHZ
(PHILOU Zrealone from the Science Madness forum)

[@ChemDungeon]

@@philouzlouis2042 thank you! coincidentally enough, that’s exactly the synthetic method I plan on doing to make it, I got the last reagent I needed for it in the mail a few days ago. Hopefully the inclusion of ferrous sulfate reduces the notorious violence of the reaction. Otherwise, I might use a modified method that uses As2O3 and omits nitrobenzene that’s supposedly not violent at all. Time will tell, I’ll be doing a trial run in a day or 2 depending on how long it takes to purify my aniline and edit the video I’ve been working on in the meantime

[@dimaminiailo3723]

@@ChemDungeon Use the procedure from OrgSyn, they're always incredibly reliable and repeatable (you most likely know it, but just in case). It's best to not use As2O3 because if its rarity and certain disposal issues. The steam distillation in the procedure may be carried out using a Dean-Stark trap instead as to not collect insane amounts of distillate, but it would take a correspondingly longer time. If you desire to accelerate the distillation rather than ease your life a bit, I advise to employ a pressure cooker as the source of steam (the condenser should be chosen appropriately)

[@ChemDungeon]

@@dimaminiailo3723 That's exactly the procedure I'm using! It worked well enough in the smaller scale (1/20 that of orgsyn) trial run that I'm currently filming the larger scale (1/5 that of orgsyn) run now. I had the same exact thought about the Dean-Stark trap, but I chose to only use it for the last steam distillation that I did last night just so I could test out a new "traditional" steam distillation apparatus in all the ones leading up to it. Overall, it took quite a while, but I think I'll do Dean-Stark steam distillations for most of the steps in this larger scale synthesis to avoid collecting liters upon liters of distillate. It also has the added benefit of much more easily monitoring the endpoint of the distillation because once the condensate in the trap goes clear, it's not worth collecting anything more. The pressure cooker steam generator is a good idea, I have another method that I think works equally well if not better, you'll see it in the video :)

[@dimaminiailo3723]

@@ChemDungeon I would rather run the full-scale synthesis and store spare quinoline in its salt form, which is virtually 'immortal' and easily converted into pure quinoline. The only thing I can think of that can rival a pressure cooker on an induction plate for generating a considerable amount of steam in a short time is a repurposed steam train (x_x ;)

[@ChemDungeon]

@@dimaminiailo3723 I’d run it on the orgsyn scale if I had a 5L flask and heating mantle, but I don’t, so I had to go with 1/5 scale to work with my 1L flask, etc. What I do hasn’t necessitated anything larger than a 1L flask so far :p maybe I should invest in some bigger glassware and equipment. It’s definitely not a repurposed steam train, I’ll say that much

[@midwestchem368]

This is a reaction i havent came across yet. Very cool video man!!!

[@ChemDungeon]

@@midwestchem368 it is kinda obscure, especially for home chemists since it uses cyanide and quinoline. Thanks brother :)

[@dimaminiailo3723]

Thank you for showing such a rare synthesis. I believe your quinoline was of acceptable purity, I'd perform no more than a steam distillation and one or two vacuum fractional ones, depending on the stability of its bp.

[@ChemDungeon]

Of course :) I can't think of any other reason the yield would be as low as it was since I followed the procedures to a T. The purity of my quinoline seems to be the only possible discrepancy unless it was acceptably pure, in which case the yields just aren't as high as those reported in the literature

[@bryce4359]

First