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ChemicalBook CAS DataBase List 7-Chloro-2-methylquinoline
4965-33-7

7-Chloro-2-methylquinoline synthesis

11synthesis methods
Ethyl vinyl ether

109-92-2

3-Chloroaniline

108-42-9

7-Chloro-2-methylquinoline

4965-33-7

To a 50 mL round-bottomed flask equipped with a condenser and a PTFE stirrer was added m-chloroaniline (1 mmol), acetonitrile (5 mL), Catalyst 1 (10 mol%), and vinyl ether (3 mmol). The reaction mixture was heated in air at 80 °C for the reaction time referred to Table 1. The progress of the reaction was monitored by thin layer chromatography (TLC). Upon completion of the reaction, the solvent was removed by distillation under reduced pressure and the residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate) to afford 7-chloro-2-methylquinoline. The structure of the product was confirmed by comparing the spectral data reported in the literature.

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Yield:4965-33-7 90%

Reaction Conditions:

with chloro[1,3-bis(2,6-di-i-propylphenyl)imidazol-2-ylidene]copper(I);sodium t-butanolate in toluene at 70;Inert atmosphere;Schlenk technique;chemoselective reaction;

References:

Zhang, Song-Lin;Deng, Zhu-Qin [Organic and Biomolecular Chemistry,2016,vol. 14,# 38,p. 8966 - 8970] Location in patent:supporting information

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