Large-Scale Synthesis of 2-Chlorotetrahydroquinoline and 2-Chlorotetrahydroquinolin-8-one

Synthesis ◽  
2020 ◽  
Vol 52 (23) ◽  
pp. 3675-3683
Author(s):  
Liqun Jin ◽  
Xinquan Hu ◽  
Zhijian Zong ◽  
Ke Wu ◽  
Nan Sun ◽  
...  

An efficient large-scale preparation of 2-chlorotetrahydroquinoline with cyclohexanone and benzylamine as starting materials was developed and well optimized, in which benzyl-protected enamide was successfully cyclized and benzyl group was directly removed under Vilsmeier conditions. Azeotropic distillation provided 264 g of 2-chlorotetrahydroquinoline (79%) on a 2 mol scale of reaction without intermediate isolation. The downstream product 2-chlorotetrahydroquinolin-8-one was acquired through Boekelheide rearrangement, hydrolysis of acetate via NaBH4 reduction, and Anelli oxidation. With the developed procedure, the intermediates were not necessary to be isolated and 2-chlorotetrahydroquinolin-8-one was conveniently obtained with solvent slurry in 65% overall isolated yield in a four-step sequence.

RSC Advances ◽  
2015 ◽  
Vol 5 (72) ◽  
pp. 58889-58894 ◽  
Author(s):  
Jianan Zhang ◽  
Zhengquan Lu ◽  
Mingyuan Wu ◽  
Qingyun Wu ◽  
Jianjun Yang

A facile method for the large-scale preparation of poly(acrylic acid) (PAA) nanogels was reported by miniemulsion polymerization. After the encapsulation of magnetic nanoparticles, magnetic PAA nanogels were fabricated successfully.


1969 ◽  
Vol 22 (03) ◽  
pp. 577-583 ◽  
Author(s):  
M.M.P Paulssen ◽  
A.C.M.G.B Wouterlood ◽  
H.L.M.A Scheffers

SummaryFactor VIII can be isolated from plasma proteins, including fibrinogen by chromatography on agarose. The best results were obtained with Sepharose 6B. Large scale preparation is also possible when cryoprecipitate is separated by chromatography. In most fractions containing factor VIII a turbidity is observed which may be due to the presence of chylomicrons.The purified factor VIII was active in vivo as well as in vitro.


1992 ◽  
Vol 70 (6) ◽  
pp. 448-454 ◽  
Author(s):  
Ewa Świeżewska ◽  
T. Chojnacki ◽  
W. J. Jankowski ◽  
K. Singh ◽  
J. Olsson

The long chain polyprenols composed of 30 and more isoprene units from leaves of plants belonging to the genera Potentilla and Rosa have been described. They occur in the form of fatty acid esters. The composition of polyprenol mixture was species dependent and its content reached ca. 0.5% wet weight. Large scale preparation of individual polyprenols from a natural polyprenol mixture was performed using time-extended liquid chromatography on the hydrophobic gel Lipidex-5000.Key words: long chain polyprenols, Rosaceae.


Soft Matter ◽  
2018 ◽  
Vol 14 (6) ◽  
pp. 1043-1049 ◽  
Author(s):  
Yanyan Feng ◽  
Yujia Wan ◽  
Ming Jin ◽  
Decheng Wan

We show here the first example of the large-scale surface decoration of a macroscopic and porous monolith with dissimilar micropatches.


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