Skraup reaction process for synthesizing quinolones - …

Solketal is derived from the reaction of acetone with glycerol, a by-product product of the biodiesel industry. We report here the continuous reaction of solketal with anilines over a solid acid niobium phosphate (NbP), for the continuous generation of quinolines in the the well-established Skraup reaction. This study shows that NbP can catalyse all stages of this multistep reaction at 250 °C and 10 MPa pressure, with a selectivity for quinoline of up to 60%. We found that the catalyst eventually deactivates, most probably via a combination of coking and reduction processes but nevertheless we show the promise of this approach. We demonstrated here the application of our approach to synthesize both mono- and bis-quinolines from the commodity chemical, 4,4’-methylenedianiline.

New syntheses of 5,6- and 7,8-diaminoquinolines

Continuous niobium phosphate catalysed Skraup reaction …

Synthesis of Quinolines, Chemistry tutorial - TutorsGlobe

Mitsunobu reaction…
The never discussed problem with this reaction is that it requires excess reacgents. Someone find an example in the literature where someone was using only 1 equivalent of reagent and/or nucleophile….And don’t get me started about having to get rid of triphenylphosphine oxide and hydrazide byproducts.
You could also fill a book with examples where the reaction doesn’t work or gave an alternative product.

Study on the Synthesis of Quinoline Intermediates for Pharmacology ..

Your comments on the Skraup reaction reminded me of a grad student classmate. He tried many Skraup reactions and never had much success. He finally changed the name of the reaction from “the Skraup reaction” to “the Screw-up reaction.”


21/10/2010 · Skraup synthesis

Equation 8-3 is used to convert the frequency domain signal, (b), into theamplitudes of the cosine waves, (c). As shown, all of the cosine waves have anamplitude of , except for samples 0 and 16, which have a value of . Theamplitudes of the sine waves are not shown in this example because they havea value of zero, and therefore provide no contribution. The synthesis equation,Eq. 8-2, is then used to convert the amplitudes of the cosine waves, (b), into thetime domain signal, (a).

CHE Syllubus | Chemical Reactions | Coordination Complex

Methods for the batch scale up of DABAL-Me3 promoted direct ester to amide synthesis have been demonstrated at 10–100 g scales using a -amide model compound. Procedures for 20 g scale couplings in standard laboratory glassware and up to 0.1 kg in industry-standard jacketed glass reactors in near quantitative yields are given. A derivative of the anticancer agent Imatinib (Gleevec) has been synthesized on a 26 g scale (98% yield, >98% purity) establishing DABAL-Me3 as a potential alternative for the synthesis of amides in API scale preparations. Continuous flow methodology provides a method for larger scales (productivities of >50 g h–1). In addition, nitriles were coupled to primary amines and hydrazines with DABAL-Me3, resulting in the clean formation of free amidines (16 examples) and amidrazones.

mesityl oxide, 141-79-7 - The Good Scents Company

“What is it about SN2 or alkyl halide coupling that Grignards can’t do? Is it just the electronics of the situation?”
Chemist of sorts in #46 is very right. The copper salt protocol I find works best is 10 mol% of CuI. Add at -30 degrees Celsius and keep the temperature at -23 for an hour or two (this is very important), and most couplings with Grignards will work for me. Of course, then you have a lot of copper salts in your workup mixture that you have to dissolve with strong base.

pulegone 15932-80-6 - The Good Scents Company

The DIBAL-H low temp reduction of an ester to an aldehyde has certainly been blacklisted in my book. Good example of textbook Ochem reaction that just doesn’t work well in practice. Nearly every time I tried it, I get mixtures of aldehyde and alcohol. So much easier (and better yield) to take the ester to the alcohol and back up to the aldehyde.

This is a complete assignment on Quinoline

The direct and selective synthesis of phenols from aryl/heteroaryl halides and KOH has been achieved through the use of highly active monophosphine-based catalysts derived from Pd2dba3 and ligands L1 or L2 and the biphasic solvent system 1,4-dioxane/H2O. We have also demonstrated a one-pot method of phenol formation/alkylation for the preparation of alkyl aryl ethers from aryl halides. In many instances, this protocol overcomes limitations in existing Pd-catalyzed coupling reactions of aliphatic alcohols with aryl halides. Finally, we demonstrate that substituted benzofurans can be prepared efficiently via a Pd-catalyzed phenol formation/cyclization protocol starting from 2-chloroaryl alkynes.