4-Toluenesulfonyl chloride → 3,3-Dimethyl-2-(4-(4-methylphenylsulfonamido)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylic acid

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Reaction Steps

To a solution of 2-(4-aminophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid (80 mg, 0.27 mmol) in pyridine (5 mL) was added 4-methylbenzene-1-sulfonyl chloride (57 mg, 0.30 mmol) with ice cooling. Upon completion of the addition, the resultant mixture was allowed to warm back to room temperature and stir overnight. LC-MS showed the reaction was complete. Pyridine was removed in vacuo and the residue was purified by preparative Thin layer chromatography to afford 70 mg of 3,3-dimethyl-2-(4-(4-methylphenylsulfonamido)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylic acid as a yellow powder. Yield: 69%; MS (ESI+APCI) M+1=451.20.

Provenance & Evidence