Arsenic Acid → 6-[4-(7-Phenyl-1,10-phenanthrolin-4-yl)phenyl]hexan-1-ol

Participants

Reaction Steps

The procedure followed was similar to that of Case and Strohm (Case, F. H.; Strohm, P. F. J. Org. Chem, 1962, 27, 1641-1643). 3-Chloro-1-[4-(6-hydroxyhexyl)phenyl]propan-1-one (0.73 g), 8-amino-4-phenylquinoline (0.27 g), arsenic acid (0.99 g) and 85% phosphoric acid (10 mL) were reacted as described in the procedure for the synthesis of 8-nitro-4-phenylquinoline. However during precipitation of the crude product, a pH of 6-8 was maintained in order to ensure that the alcohol functionality remained protonated. The crude product was re-crystallized with a 50:50 mixture of petroleum ether and chloroform. Further purification of the desired product was achieved using preparatory TLC with 2% methanol and 98% chloroform.

Provenance & Evidence