C(Cl)(=O)C([Cl:4])=O.[CH3:7][N:8]1[C:17]2[C:12](=[CH:13][C:14]([S:18]([OH:21])(=O)=[O:19])=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1>ClCCl.CN(C=O)C>[CH3:7][N:8]1[C:17]2[C:12](=[CH:13][C:14]([S:18]([Cl:4])(=[O:21])=[O:19])=[CH:15][CH:16]=2)[CH2:11][CH2:10][CH2:9]1Oxalyl chloride (20 g, 157.60 mmol) was added dropwise at room temperature to a solution of 1-methyl-1,2,3,4-tetrahydroquinoline-6-sulfonic acid (5 g, 22.00 mmol) in dichloromethane (100 mL) and DMF (10 mL). The resulting solution was stirred for 2 hours, then quenched by adding 200 mL of iced water. The resulting solution was extracted using dichloromethane (2×100 mL), and the combined organics were dried (Na2SO4), filtered and concentrated. The residue was purified by column chromatography using a 1:4 ethyl acetate/petroleum ether solvent system to afford 1.1 g (20.1%) of 1-methyl-1,2,3,4-tetrahydroquinoline-6-sulfonyl chloride as a yellow solid. 1H NMR (CDCl3) δ 7.69 (d, 1H), 7.51 (s, 1H), 6.54 (d, 1H), 3.57 (t, 2H), 3.02 (s, 3H), 2.78 (d, 2H), 1.98 (m, 2H).
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