2-Nitrobenzaldehyde → HCID 14676008, compound

Participants

Reaction Steps

o-Nitrobenzaldehyde (3.8 g, 0.025 mole), n-pentyl 3-aminocrotonate (4.3 g, 0.025 mole) and acetoacetic isopropylamide (3.6 g, 0.025 mole) are dissolved in ethanol (50 ml), and the mixture is refluxed for 8 hours. After the reaction, the solvent is distilled off under reduced pressure. The residue is dissolved in elution solvent [chloroform:carbon tetrachloride:ethyl formate:formic acid:ethanol (10:10:8:1:2)] (30 ml) and subjected to column chromatography [silica gel 60 Art. 9385 (Manufactured by Merck Co.), 300 g, φ40 mm×50 cm]. The fraction containing the desired compound is regulated to pH 10 with 28% aqueous ammonia, and the organic layer is separated, washed with water, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue is recrystallized from 80% ethanol to give the title compound (3.2 g, yield 30.0%) as yellow prisms, m.p. 186°-189° C.

Provenance & Evidence