(4-Aminophenoxy)benzene → (4-Phenoxyphenyl)-(7-iodoquinolin-4-yl)amine

Participants

Reaction Conditions

Reaction Steps

4-Chloro-7-iodoquinoline (10 g, 34 mmol) [Semenov, V. P.; Studenikov, A. N. Synthesis of 7-iodo-4-aminoquinoline derivatives. Khim. Geterotsikl. Soedin. (1980), Issue 7, 972-5] and 4-phenoxyaniline (6.38 g, 34 mmol) in butanol (75 ml) were heated at gentle reflux (120° C.) overnight (18 hrs). On cooling the resultant precipitate was collected by filtration and washed with acetonitrile (2×50 ml). The resultant solid was suspended in chloroform (500 ml) and 2N sodium carbonate solution (300 ml) and heated at 75° C. for 45 mins. On cooling the resultant precipitate was collected by filtration, washed with water (2×50 ml) and dried to yield the product as a pale brown solid. (9.95 g, 66%) δH [2H6]DMSO 8.35(3H, m), 8.20(1H, s), 8.10(1H, d), 7.85(1H, s), 7.35(4H, m), 7.15(4H, d), 6.75(1H, d).

Provenance & Evidence