p-Toluenesulfonic acid → HCID 178470446, compound

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Reaction Steps

A mixture of ethyl 6-amino-4-hydroxycinnolin-3-yl carboxylate (0.932 g.), 5,5-dimethylcyclohexan-1,3-dione (2.24 g.) and p-toluenesulphonic acid (0.4 g.) in ethanol (100 ml.) was heated under reflux on a steam bath for 16 hours. The solution was evaporated in vacuo and the residue was applied to a silica column (100 g. Kieselgel 60). Elution with a mixture of 15% v/v ethanol and 85% v/v chloroform, and evaporation of the appropriate fractions gave crystalline ethyl 6-[(5,5-dimethylcyclohexen-3-one-yl)amino]-4-hydroxycinnolin-3-yl carboxylate, m.p. 274° C.

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