Hydrochloric Acid → 2-Quinolinecarboxylic acid,1-[2-(benzoylthio)-1-oxopropyl]-1,2,3,4-tetrahydro-

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Reaction Steps

(±)-1,2,3,4-Tetrahydro-2-quinolinecarboxylic acid hydrochloride (43 g) in pyridine (300 ml) was treated dropwise with 2-benzoylthiopropanoyl chloride (46 g) with vigorous stirring. After stirring at room temperature overnight, the mixture was poured onto ice (300 g) and acidified with concentrated hydrochloric acid. The product was extracted with ether and the ether extracts combined, dried over sodium sulfate, and concentrated to dryness in vacuo. The residue, (±)-1-(2-benzoylthio-1-oxopropyl)-1,2,3,4-tetrahydro-2-quinolinecarboxylic acid, was crystallized from acetonitrile (100 ml); yield 7 g, m.p. 157°-159°.

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