2,3-Dichlorobenzaldehyde → HCID 13457175, compound

Participants

Reaction Steps

A solution of 2,3-dichlorobenzaldehyde (8.75 g), methyl 3-aminocrotonate (5.75 g) and ethyl 4-[2-(2,4,5-trimethyl-1-imidazolyl)ethoxy]acetoacetate (14.1 g) in 50 ml of methanol was stirred at reflux temperature for 5 hours. After evaporation to dryness, the residue was dissolved in 2N hydrochloric acid (200 ml) and washed with diethyl ether (3×100 ml) followed by extraction with methylene chloride (4×150 ml). The combined methylene chloride extracts were washed with saturated aqueous sodium carbonate solution (2×200 ml), dried (Na2CO3), filtered and evaporated to give a beige solid (12.5 g). The crude product was chromatographed on silica (40 g), eluting with ethyl acetate. The appropriate fractions were combined and evaporated and the resultant oil (2.1 g) crystallised from diethyl ether (10 ml) to give the title compound, (1.5 g), m.p. 123°-125° C.

Provenance & Evidence