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ChemicalBook CAS DataBase List 6-Fluoroquinaldine
1128-61-6

6-Fluoroquinaldine synthesis

10synthesis methods
6-Fluoro-1,2,3,4-tetrahydro-2-methylquinoline

42835-89-2

6-Fluoroquinaldine

1128-61-6

General procedure for the synthesis of 6-fluoro-1,2,3,4-tetrahydro-2-methylquinoline from 6-fluoro-1,2,3,4-tetrahydro-2-methylquinoline: 6-fluoro-1,2,3,4-tetrahydro-2-methylquinoline (0.50 mmol), FeCl2 (1.9 mg, 1.5 × 10-2 mmol), DMSO (31.2 mg, 0.4 mmol) and p-xylene (1 mL). The reaction mixture was stirred using a balloon at 110 °C and oxygen atmosphere and the progress of the reaction was monitored by TLC. Upon completion of the reaction, the mixture was cooled to room temperature and purified by fast chromatography (eluent: hexane-ethyl acetate, 10:1) to afford the target product 6-fluoro-2-methylquinoline in 70% yield. 6-fluoro-2-methylquinoline was a colorless oil.1H NMR (400 MHz, CDCl3): δ = 8.93 (m, 1H), 8.10 (m, 1H) , 7.64 (d, J=4.0 Hz, 1H), 7.54 (m, 1H), 7.43-7.35 (m, 2H), 2.82 (s, 3H).13C NMR (100 MHz, CDCl3): δ=149.2, 147.3, 137.1, 136.3, 129.6, 128.3, 126.3, 125.9. 120.8, 18.2. HRMS: m/z calculated value of [C10H9FN+H]+: 144.0813; measured value: 144.0813.

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Yield:1128-61-6 75%

Reaction Conditions:

with transition metal catalyst;pyridine derviative;acid derviative at 150; for 18 h;Green chemistry;

Steps:

8
Accurately weigh 0.005mmol (l. Lmg) of the transition metal, add 10mL has been put into the magnetic stirrer Young's reaction tube, The oxygen reaction was carried out in the Young's reaction tube, and the reaction was carried out under oxygen conditions. The syringe was applied to the Young's reaction tubeAdd 0.04 mmol of co-catalyst I, 0.08 mmol of co-catalyst II, 0.2 mmol of 4-fluoroaniline and 1 ml of absolute ethanol,The above-mentioned Young's reaction tube was placed on a magnetic stirrer and stirred at 150 ° C for 18 hours. After the completion of the reaction, the pH of the reaction solution was adjustedThe reaction solution was post-treated to give pure 2-methyl-6-fluoro-quinoline in 75% yield.

References:

Suzhou Research Institute, Lanzhou Institute of Chemical Physics (LICP) of the Chinese Academy of Sciences (CAS);Jiang, Gaoxi;Li, Jixing;Yang, Huimeng;Xia, Chungu CN106543078, 2017, A Location in patent:Paragraph 0073; 0074

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