4-Chloro-7-(3-chloropropoxy)-6-methoxyquinoline-3-carbonitrile → 4-(6-Chloro-2,3-methylenedioxyanilino)-7-(3-chloropropoxy)-3-cyano-6-methoxyquinoline

Participants

Reaction Conditions

Reaction Steps

Sodium hexamethyldisilazane (1M solution in THF; 3.34 ml) was added to a solution of 6-chloro-2,3-methylenedioxyaniline (0.573 g) in DMF (12 ml) that was cooled to 0° C. and the mixture was stirred for 5 minutes. A solution of 4-chloro-7-(3-chloropropoxy)-3-cyano-6-methoxyquinoline (0.5 g) in DMF (3 ml) was added and the resultant mixture was stirred at ambient temperature for 1 hour. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic phase was washed with water and with brine, dried over magnesium sulphate and evaporated. The residue was purified by column chromatography on silica increasingly polar mixtures of methylene chloride and ethyl acetate as eluent. There was thus obtained the title compound as a solid (0.62 g); NMR Spectrum: DMSOd6 at 60° C.) 2.32 (m, 2H), 3.9 (m, 2H), 4.0 (s, 3H), 4.35 (m, 2H), 6.1 (s, 2H), 7.0 (d, 1H), 7.1 (d, 1H), 7.4 (s, 1H), 7.9 (s, 1H), 8.42 (s, 1H), 9.32 (s, 1H); Mass Spectrum: M+H+ 446 and 448.

Provenance & Evidence