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ChemicalBook CAS DataBase List 7-NITRO-QUINOLINE
613-51-4

7-NITRO-QUINOLINE synthesis

14synthesis methods
7-Nitro-1,2,3,4-tetrahydroquinoline

30450-62-5

7-NITRO-QUINOLINE

613-51-4

7-Nitro-1,2,3,4-tetrahydroquinoline (60 g, 0.337 mol) was used as raw material and dissolved in dichloromethane (4.5 L). Dichlorodicyanobenzoquinone (152.9 g, 0.6734 mol) was added in batches at room temperature and the reaction was stirred for 1 hour. After completion of the reaction, filtration was carried out and the filter cake was washed with dichloromethane (500 mL x 2) and stirred for 5 min each time before filtration again. The organic phases were combined and washed sequentially with 10% sodium hydroxide solution (500 mL x 2) and saturated sodium chloride solution (500 mL). The organic phase was dried over anhydrous sodium sulfate and concentrated to dryness under reduced pressure. The resulting orange solid was stirred with a solvent mixture of petroleum ether:ethyl acetate (5:1, 250 mL) for 30 min, and 7-nitroquinoline (53 g, 90.3% yield) was obtained after filtration.

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Yield: 25.8 %Chromat.

Reaction Conditions:

with Ni-modified Beta zeolite in neat (no solvent) for 0.0833333 h;Microwave irradiation;Reflux;Green chemistry;

Steps:

2.2. Catalytic performance evaluation
General 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).

References:

Li, An;Yang, Zan;Yang, Tao;Luo, Cai-Wu;Chao, Zi-Sheng;Zhou, Cong-Shan [Catalysis Communications,2018,vol. 115,p. 21 - 25]

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