Chloromethyl acetate → Acetyloxymethyl 2-acetylnicotinate 4-(3-fluorophenyl)semicarbazone

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Reaction Steps

A mixture of the sodium salt of compound 4 (1.0 g, 3.0 mmol) and chloromethyl acetate (0.4 g, 3.5 mmol) in 18 ml of DMF is stirred at RT for 3 days. The reaction mixture is poured onto ice. The solid which precipitates is collected by filtration, is washed with water and is air-dried. It is stirred in 50 ml of chloroform for 2 hours and is filtered. The filtrate is evaporated to give glass-like material, which is triturated with ether to give the crude product. Purification by prep. TLC gives acetyloxymethyl 2-acetylnicotinate 4-(3-fluorophenyl)semicarbazone, m.p. 159°-160° (compound 54, Table C).

Provenance & Evidence