Ethanol → Ethyl 5-chloroquinoline-6-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of ethyl 4-amino-2-chlorobenzoate (20 g), glycerol (32.17 g) and sodium 3-nitrobenzenesulfonate (46.73 g) in sulfuric acid (75%) (160 ml) was stirred for 3 hours at 100° C. and for 1 hour at 140° C. After the mixture was cooled to 60° C. and ethanol (200 ml) was added, the mixture was stirred for 16 hours at 60° C. Ethanol was evaporated and the residue was poured into ice water, neutralized with NH4OH and extracted with ethylacetate. The separated organic layer was dried over MgSO4, filtered and the filtrate evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /ethylacetate 97.5/2.5). The desired pure fractions were collected and evaporated, yielding 7.56 g (28%) ethyl 5-chloro-6-quinolinecarboxylate (intermediate 1).

Provenance & Evidence