4-[(3-Chlorophenyl)amino]-6-nitro-3-quinolinecarbonitrile → 6-Amino-4-(3-chlorophenylamino)quinoline-3-carbonitrile

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Reaction Steps

A mixture of 6.30 g (19.4 mmol) 4-[(3-chlorophenyl)amino]-6-nitro-quinoline-3-carbonitrile, 300 ml ethanol, and 21.9 g (97 mmol) SnCl2 dihydrate were heated to reflux under N2. Removed heat at 2½ hours, added ice water and made basic with sodium bicarbonate. Stirred for 2 hours and extracted with chloroform. Dried organic layer with sodium sulfate, filtered, stripped solvent and dried residue in vacuo, giving 5.74 g of yellow-brown solid: mass spectrum (electrospray m/e): M+H=295.1, 297.1.

Provenance & Evidence