7-Nitroquinoline

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 CHClIn the reactor, 100 mg of substrate 7-nitro-1, 2, 3, 4-tetrahydroquinoline, 10mg boron carbonitriding photocatalyst, 3ml of water and 1.2 equivalents of cesium fluoride, stirred at room temperature for 24 hours under light irradiation, after the reaction was extracted with ethyl acetate, the combined organic phase was dried, filtered and the solvent was evaporated under reduced pressure to give the crude product, The column chromatography eluant used was a petroleum ether: ethyl acetate mixed solvent in a volume ratio of 1: 1 with a yield of 91percent.Dichloromethane (4.5 L) was added to 7-nitro-1, 2, 3, 4 tetrahydroquinoline (60 g, 0.337 mol), and dichlorodicyanobenzoquinone (152.9 g, 0.6734 mol) was added portionwise. ), stirring at room temperature for 1 h, suction filtration, The filter cake was stirred with dichloromethane (500 mL * 2) for 5 min, suction filtered;Wash with 10percent NaOH (500mL*2), Wash with saturated NaCl solution (500 mL), The organic phase was dried over anhydrous Na2SO4 and evaporated to dryness.The concentrated orange solid was stirred with a solvent of petroleum ether: ethyl acetate = 5:1 (250 ml) for 30 min and filtered to afford 7-nitroquinoline (53 g, 90.3percent).7-aminoquinoline was prepared according to the following reaction in scheme 14.General procedure: DDQ (114mg, 0.5mmol) was added to the stirred solution of secondary amine 1 (0.50mmol) and phosphite (0.75mmol) in THF (1mL) at room temperature. The resulting mixture was kept stirring at 80°C for 4h. Subsequently, the mixture was poured into aqueous NaGeneral 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).Following the procedure described by Filippi, J. (Bull. Soc. Chim. Fr. 1968, 1, 259-67). [00200] The Skraup reaction of m-nitroaniline and glycerol in the presence of As2O3 and H2SO4 afforded a 65:35 mixture of 5-nitroquinoline and

Molecular Weight:174.16
XLogP3:1.8
Hydrogen Bond Acceptor Count:3
Exact Mass:174.042927438
Monoisotopic Mass:174.042927438
Topological Polar Surface Area:58.7
Heavy Atom Count:13
Complexity:202
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes