Ethyl Acetate → 3,3-Dimethyl-2-(3-(1-methylethylsulfonamido)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylic acid

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Reaction Steps

2-(3-Aminophenyl)-3,3-dimethyl-1,2,3,4-tetrahydroquinoline-6-carboxylic acid (100 mg, 0.34 mmol) was dissolved in 2 mL of dry pyridine under nitrogen. Then propane-2-sulfonyl chloride (0.1 mL, 0.89 mmol) was added drop wise to the reaction mixture. The reaction mixture was allowed to stir overnight. Thin layer chromatography (petroleum ether:ethyl acetate=1:1, Rf=0.5) showed the reaction was complete. Pyridine was removed in vacuo and the residue was purified by column chromatography (petroleum ether:ethyl acetate=1:1) to afford 50 mg of 3,3-dimethyl-2-(3-(1-methylethylsulfonamido)phenyl)-1,2,3,4-tetrahydroquinoline-6-carboxylic acid. Yield: 36.8%. MS (ES+APCI) M+1=403.1.

Provenance & Evidence