ChemicalBook CAS DataBase List 6-Bromoquinoline

6-Bromoquinoline synthesis

10synthesis methods

Product Name:6-Bromoquinoline
CAS Number:5332-25-2
Molecular formula:C9H6BrN
Molecular Weight:208.05

4-Bromobenzenamine (25 g, 145.32 mmol, 1.00 equiv), sodium 3-nitrobenzenesulfonate (55.5 g, 246.64 mmol, 1.70 equiv), propane-1,2,3-triol (50.8 g, 551.63 mmol, 3.80 equiv), and sulfuric acid (170 mL, 70%) were placed into a 500-mL round-bottom flask. The resulting solution was stirred overnight at 140° C. The pH value of the solution was adjusted to with 10% aqueous sodium hydroxide. The resulting solution was extracted with 5*150 mL of ethyl acetate. The organic layers were combined and dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with ethyl acetate/petroleum ether (1:50). This resulted in 17.2 g (42%) of 6-bromoquinoline as yellow oil.

56-81-5 Synthesis

56-81-5
1663 suppliers
$5.00/25g

106-40-1 Synthesis

106-40-1
468 suppliers
$12.00/5g

5332-25-2
418 suppliers
$6.00/5g

Yield:5332-25-2 81%

Reaction Conditions:

with tungstic acid functionalized KIT-6 in water at 200; for 3 h;Autoclave;Skraup Quinoline Synthesis;

Steps:

General procedure for synthesis of quinolines
General procedure: All the reactions were carried out in a 50 mL stainless steel autoclave (Scheme 1). A mixture of glycerol (1 g, 1 equiv.), aniline (0.58 g, 0.5 equiv.), water (2.5 mL) and W-KIT-6 (100 mg) was charged in to the autoclave simultaneously and finally heated to 200 °C with stirring for 3 h. On completion of the reaction (monitored by TLC), the autoclave was cooled to room temperature and the catalyst was removed by filtration. Ethyl acetate (10 mL) and water (5 mL) were added to the reaction mixture and stirred well for few minutes. The organic layer was dried over anhydrous Na2SO4 and the crude was purified by column chromatography using 60-120 mesh silica with ethylacetate/hexane as eluent to afford the desired product in good yield. The product was analyzed and confirmed with GC-MS and 1H NMR and 13C NMR spectroscopy (Table 1 and Figs S1-S5, Supplementary Data).

References:

Udayakumar;Pandurangan [Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,2016,vol. 55A,# 8,p. 919 - 928]

22190-35-8 Synthesis