6-Fluoroquinoline

General procedure: To a 10 mL round bottom flask equipped with a magnetic stir bar, 1, 2, 3, 4-tetrahydroquinoline (0.5 mmol), DEAD solution 40 wtpercent in toluene (2.2 eq, 1.1 mmol, 0.5 mL), and CHClGeneral procedure: N-Heterocyclic amine (0.50 mmol), CoTPP (10 mg) and DMF (2 mL) were mixed in a carousel reaction tube. The reaction mixture was stirred at 120 C under oxygen atmosphere, the reaction was sampled periodically and monitored by TLC (petroleum ether/ethyl acetate (10:1 v/v)). After the reaction, the reaction mixture was then cooled to room temperature and purified using flash chromatography to give the corresponding product. All the dehydrogenation products are known, and their NMR spectra were consistent with the literature. NMR spectra were recorded at 25 C on an Bruker AVANCE III 400-NMR spectrometer at 400 MHz for To aryl silane (0.100 mmol, 1.00 equiv) in acetone (2.0 mL) at 23 °C were added silver oxide (69.6 mg, 0.300 mmol, 3.00 equiv), barium oxide (17.2 mg, 0.110 mmol, 1.10 equiv), and 1-chloromethyl-4-fluoro-1, 4-diazoniabicyclo-[2.2.2]octane bis(tetrafluoroborate) (1) (70.8 mg, 0.200 mmol, 2.00 equiv). The reaction mixture was stirred for 2 h at 90 °C in a sealed vial. The reaction mixture was cooled to 23 °C, passed through a pad of Celite and concentrated under reduced pressure. To the residue was added CHGeneral procedure: General procedure for synthesis of quinolines from anilines and ADA was carried out in Panasonic NN-K5541JF microwave oven reactor equipping a magnetic stirring device. The typical procedures were as follows: ADA (1mmol), excessive anilines (4mmol) and solid catalyst were charged into a round-bottom ask; and then, the mixtures was placed into microwave reactor. The reaction was conducted by continuous microwave irradiation for 1–40 min under refluxing and stirring condition. Finally, the resulting products were determined by GC–MS of Varian Saturn 2200/ CP-3800 gas chromatography–mass spectrometry equipped with two CP8944 capillary columns (VF-5, 30m×0.25mm×0.25 μm).Concentrated sulfuric acid (3 eq) was added dropwise to a vigorously stirred mixture of 4-fluoro aniline (1 eq), I2 (0.1 eq), in glycerol (1.5 eq) within 0.5 h, wherein the temperature of the mixture rises to 65-70 C. The mixture was then heated to 135-140 0C for 10-12 h giving dark brown forming mixture. The mixture was cooled to room temperature and quenched in ice cooled water. pH of the solution was adjusted to 8 to 9 by adding 25-30percent ammonia solution. Aqueous layer was extracted with EtOAc. Organic layer was washed with brine, dried over sodium sulfate and evaporated in vacuo to get crude product. Purification of the crude product thus obtained by the way of flash column chromatography (SiO2, 8:2 (v/v) hexane:: EtOAc) to afforded title compound as dark red liquid.In a 50 mL round-bottomed flask, 1.47 g of General procedure: To a solution of the corresponding N-heterocycles (10.0 mmol) in CH2Cl2 (20 mL), m-chloroperoxybenzoic acid (m-CPBA, 20.0 mmol, 2.0 equiv) was added at 0 C. The reaction mixture was allowed to stir at room temperature for 12 h. Then saturated aqueous NaHCO3 (20 mL) was added. The aqueous was extracted with CH2Cl2 (10 mL x 3) and the combined organic extracts were dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel with EtOAc/n-hexene or EtOAc/MeOH to afford desired N-oxides.To a solution of 6-aminoquinoline (1.0 g) in 42percent tetrafluoroboric acid (5 ml), sodium nitrite (527 mg) was added under ice cooling and stirred at the same temperature for 1 hour. After addition of diethyl ether:ethyl acetate = 1:1 (10 ml), the reaction mixture was decanted and the precipitate was dried. To the dried product, toluene (20 ml) was added and heated under reflux for 2 hours. The reaction mixture was decanted, and the resulting residue was dissolved in 1M aqueous hydrochloric acid and alkalized with saturated aqueous sodium carbonate. Insoluble materials were filtered off and the filtrate was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then filtered to remove the desiccant, followed by distilling off the solvent under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluting solvent: n-hexane:diethyl ether = 4:1 to 1:1) to give A mixture of A mixture of A mixture of (b)

Molecular Weight:147.15
XLogP3:2.2
Hydrogen Bond Acceptor Count:2
Exact Mass:147.048427358
Monoisotopic Mass:147.048427358
Topological Polar Surface Area:12.9
Heavy Atom Count:11
Complexity:138
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes