7-(Trifluoromethyl)quinoline

yellow powder

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: In the present example, BODIPY-4 in was treated with BODIPY-8 having the following structural formula (the synthesis methodBODIPY-4), and the other procedure was the same as in to obtain quinoline in a yield of 84percent.; Will replace the BODIPY organic photocatalyst(0.35 mg, 0.0005 mmol), TBAI (3.7 mg, 0.01 mmol), 1, 2, 3, 4-tetrahydroquinoline (67 mg, 0.5 mmol, Provided by Shanghai Sain Chemical Technology Co., Ltd.), N, N-dimethylformamide (5 mL) was added to the light parallel reaction tube, the oxygen balloon was bubbled for 10 minutes, the cork was screwed, the 5W blue LED was opened and the reaction was stirred at 60 ° C for 4 hours To the mixture was added 20 mL of saturated brine, and then extracted with 20 mL of ethyl acetate three times. The organic phase was collected, dried over anhydrous Na2SO4, filtered, and the solvent was removed by a rotary evaporator. Column chromatography gave a colorless oily liquid Quinoline 50 mg, the yield was 80percent, and the spectral data were4-Chloro-7-trifluoromethyl-quinoline (19.80 g, 100 mmoles) was hydrogenated in the presence of 5percent palladium on carbon in methanol in the presence of triethylamine. The solution was concentrated under reduced pressure, partitioned between ethyl acetate and water (200 mL each), separated, washed with water (2.x.200 mL), dried with magnesium sulfate, filtered and concentrated under reduced pressure to a yellow solid (7-trifluoromethyl-quinoline, 15.20 g, 90percent). H1-NMR was consistent.H2SO4 (13.7 g, 0.14 mol) was slowly added to glycerol (8.63 g, 0.094 mol).The temperature must not exceed 70 ° C, Then add m-trifluoromethylaniline (5.00 g, 0.031 mol), The temperature was raised to 85 ° C and the reaction was carried out for 40 min.Add potassium iodide (0.30 g, 1.80 mmol), (0.34 g, 1.34 mmol) of iodine, Water (1.50 mL), warmed to 135 ° C, and reacted for 4 h.After cooling to room temperature, it was poured into ice to quench the reaction and suction filtered over Celite. The filtrate was adjusted to pH 7 with aqueous ammonia, suction filtered, and the filtrate was extracted with ethyl acetate.The organic phase is dried over anhydrous sodium sulfate and concentrated.The residue was subjected to column chromatography to give 7-trifluoromethylquinoline (3.50 g, 69percent).Conc. sulfuric acid (4.56 g; 1.5 equiv.) was added dropwise to a mixture of 3-(trifluoromethyl)aniline (5 g; 1 equiv.), glycerol (5.14 g; 1.8 equiv.) and iodine (150 mg). The resulting reaction mixture was stirred for 1 hour at 80-90° C. and for 3 hours at 160-170° C. When the conversion was complete, the reaction mixture was diluted at room temperature with 100 ml of water, neutralised with sodium carbonate and extracted 4.x. with 200 ml of dichloromethane. The combined organic phases were dried over sodium sulfate, the solvent was removed under reduced pressure and the crude product was purified by column chromatography (silica gel, 10percent EtOAc/hexane). 7-(Trifluoromethyl)quinoline (1.35 g; 22.13percent) was obtained in the form of a white crystalline solid.

Molecular Weight:197.16
XLogP3:3
Hydrogen Bond Acceptor Count:4
Exact Mass:197.04523368
Monoisotopic Mass:197.04523368
Topological Polar Surface Area:12.9
Heavy Atom Count:14
Complexity:202
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes