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33644540425
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note
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The rapid stirring was crucial for the success of the reaction; otherwise, the reaction either progressed very slowly or completely ceased. A mixture of 4-chloroquinoline and silver thiocyanate in anhydrous toluene was stirred at 110°C for 12 h. The hot reaction mixture was filtered and washed three times with chloroform. The filtrate was concentrated under vacuum to afford the 4-quinolinyl isothiocyanate as an off-white solid. We thank a reviewer for the suggestion of using regular toluene. Reactions 1, 5, 7 and 11 were carried out in anhydrous toluene and regular toluene side by side. No obvious differences were noted in yields and proton NMR spectra between the two sets of reactions.
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33644532474
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