Dimethylformamide → 6-Aminoquinoline-5-carbonitrile

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Reaction Steps

Nitroquinoline (5 g, 28.71 mmol) was added to a stirred solution of ethyl cyanoacetate (9.74 g, 86.13 mmol) and potassium hydroxide (4.83 g, 86.13 mmol) in N,N-dimethylformamide (87 mL). The mixture was stirred at room temperature for 22 hours. Then the solvent was removed in vacuo and the residue was hydrolyzed with chlorohydric acid (10%) at reflux for 3 hours. The mixture was basified with sodium hydroxide (10%) and extracted three times with chloroform. The organic layer was washed with brine, dried over sodium sulfate, filtered, and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (dichloromethane/methanol 95/5) to give the desired product (16a) (3.4 g, 20.1 mmol, 70%).

Provenance & Evidence