Dichloromethane → 1-Methyl-1,2,3,4-tetrahydroquinoline-7-sulfonyl chloride

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A solution of 1-methyl-1,2,3,4-tetrahydroquinoline (10 g, 68.03 mmol) in dichloromethane (20 mL) was added dropwise to HSO3Cl (80 g, 689.66 mmol) at 0-5° C., and the resulting solution was maintained at room temperature overnight. The reaction mixture was then quenched by adding 300 mL of iced water. The resulting solution was extracted using ethyl acetate (3×150 mL). The organic layers were combined, concentrated, and the residue was purified by column chromatography using a 1:20 ethyl acetate/petroleum ether solvent system to afford 1-methyl-1,2,3,4-tetrahydroquinoline-7-sulfonyl chloride as a yellow liquid in 8% yield. 1H NMR (CDCl3) δ 7.19 (d, 1H), 7.10 (d, 1H), 7.06 (s, 1H), 3.33 (t, 2H), 2.97 (s, 3H), 2.81 (d, 2H), 1.99 (m, 2H).

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