Ethyl Acetoacetate → HCID 12713139, compound

Participants

Reaction Steps

According to this invention, water-soluble coumarins and azacoumarins having the structures: ##STR2## wherein R is CH3 or CF3 and wherein R1 is H or CH3 are prepared. The coumarins are prepared by means of a three step process involving (1) heating resorcinol and benzylamine to form 3-benzylaminophenol, (2) reacting the 3-benzylaminophenol with ethyl acetoacetate or ethyl trifluoroacetoacetate in the presence of anhydrous zinc chloride and absolute ethanol to form 7-benzylamino-4-methylcoumarin or 7-benzylamino-4-trifluoromethylcoumarin, (3) sulfonating the product of step (2) with oleum and (4) neutralizing the sulfonate formed in step (3) with sodium bicarbonate. The azacoumarins are prepared by a similar process except that 6-chloro-2-pyridinol and either benzylamine or benzylmethylamine are used as the starting compounds (the step (1) reactants).

Provenance & Evidence