Toluene → HCID 178492346, compound

Participants

Reaction Steps

230 ml of a toluene solution of triisobutyl aluminum were added with stirring at 8°-10° C. over 30 minutes to a mixture of 61.5 gof p-anisidine in one liter of anhydrous methylene chloride and then 21.7 gof ethyl 4-hydroxy-3-quinoline-carboxylate [described in J.A.C.S., Vol. 68 (1946), p. 1264] were added to the mixture in small portions. The mixture was refluxed for 20 hours and was evaporated to dryness. The residue was taken up in a mixture of 500 g of ice and 500 ml of aqueous 6 N hydrochloric acid and the mixture was stirred for 6 hours and vacuum filtered. The recovered product was washed with water until there were no chloride ions in the wash water, dried at 100° C. and was crystallized from acetic acid to obtain 23.54 g of 4-hydroxy-N-(4-methoxyphenyl)-3-quinoline-carboxamide melting at >260° C.

Provenance & Evidence