Description
4-Methyl-2-chloro-quinoline is an organic intermediate. It has been reported that it can be used to prepare graphite electrodes based on CrO-FeO-PbO and quinoline modified and a modified vermiculite adsorbent for the adsorption and removal of benzene in chemical wastewater.
Preparation
The mixture of 2-hydroxy-4-methylquinoline and phosphorus oxychloride was heated to 80-85°C. After the solid was completely dissolved, the mixture was poured into ice water, the mixture was extracted with ether, and the ether extract was distilled out of ether. Afterwards, carry out vacuum distillation, collect 132-135 ℃ (0.4kPa) fraction, namely 2-chloro-4-methylquinoline. For further purification, petroleum ether (boiling point 40-50°C) can be used for recrystallization, and the yield is 86%-89%.
Chemical Properties
white to light yellow crystal powder
Uses
2-Chloro-4-methyl-quinoline is a useful synthetic intermediate. It is an intermediate used to synthesize 4-Methyl-2-(1-piperidinyl)-quinoline (M320715) which is a potent inhibitor of TRPC4 channels, responsible for various stimulation, muscle response due to interaction with the environment. 2-Chloro-4-methyl-quinoline is also considered as a cyanine dye.
Synthesis Reference(s)
Journal of the American Chemical Society, 63, p. 2367, 1941
DOI: 10.1021/ja01854a016Organic Syntheses, Coll. Vol. 3, p. 194, 1955
Synthesis
General method: 4-Methylquinoline-N-oxide (1.0 eq.) was dissolved in anhydrous dichloromethane (0.1 M) at 0 °C. Phosphorous trichloride (1.2 eq.) was added slowly with stirring, followed by the addition of N,N-dimethylformamide (0.5 eq.) dropwise under argon protection. The reaction mixture was gradually warmed to 25 °C with continuous stirring until the reaction was complete (monitored by TLC). After completion of the reaction, saturated aqueous sodium carbonate solution was slowly added and the pH was adjusted to 7~8. The aqueous phase was extracted with dichloromethane, the organic phases were combined, washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the organic phase was concentrated under reduced pressure to obtain the crude product. The crude product was purified by fast column chromatography using petroleum ether/ethyl acetate (80:1) as eluent to obtain 2-chloro-4-methylquinoline.
References
[1] Tetrahedron Letters, 2014, vol. 55, # 51, p. 7130 - 7132
