2-Chlorophenylhydrazine hydrochloride → HCID 118431868, compound

Participants

Reaction Conditions

Reaction Steps

4-(4-Bromo-phenyl)-2-oxo-3-butenoic acid methyl ester (13.5 g, 50.2 mmol) prepared in Step 2 and 2-chlorophenylhydrazine hydrochloride (9.9 g, 55.2 mmol) were added to acetic acid (200.0 mL). The reaction mixture was stirred at 125° C. for 4 hours, concentrated under reduced pressure, and then ethyl acetate was added thereto. The reaction mixture was washed with a saturated solution of sodium hydrogen carbonate, dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure to give a yellow liquid residue. The resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/5) to give 18.9 g of the titled compound as a brown liquid.

Provenance & Evidence