Pyrrolidine → HCID 11557630, compound

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Reaction Steps

5-Chloro-8-nitroquinoline, 5 g, was reduced, diazonized, and cyanized in the same manner as in Example 1 to produce 2.62 g (yield: 58%) of 5-chloro-8-quinolinecarbonitrile. A mixture of 1.88 g of 5-chloro-8-quinolinecarbonitrile thus prepared and 7.10 g of pyrrolidine was dissolved into 30 ml of 2-ethoxyethanol and the solution was heated under reflux for 3 hours. The solvent was evaporated, and the residue, after addition of water, was extracted with chloroform. The extract was washed with water and dried over anhydrous sodium sulfate. Chloroform was evaporated, and the residue was refined by column chromatography on silica gel using a chloroform-methanol (95:5) mixed solvent as an eluent. The crystals thus obtained were recrystallized from ethanol to yield 1.54 g (yield: 69%) of 5-pyrrolidino-8-quinolinecarbonitrile (Compound No. 7).

Provenance & Evidence