Toluene → Quinoline

Participants

Reaction Steps

N-methylpiperazine was first introduced into compound XXXXVIII which was converted to enaminoketoester L on treatment with N,N-dimethylformamide dimethyl acetal in toluene followed by the reaction with 2-amino-1-propanol in ethanol. Reaction of enaminoketoester L with potassium fluoride in DMF gave quinoline LI which was cyclized with strong base such as sodium hydride to give the ester LII. Alternatively, enaminoketoester L may be reacted with sodium hydride in dioxane to yield the ester LII which was hydrolyzed with sodium hydroxide to give Ofloxacin.

Provenance & Evidence