m-Chlorophenylhydrazine hydrochloride → HCID 58345406, compound

Participants

Reaction Steps

631.5 mg (2.15 mmol) of lithium (1Z)-4-ethoxy-3,4-dioxo-1-[3-(trifluoromethyl)phenyl]but-1-en-1-olate from example 1A are suspended in 15 ml of ethanol, 522.7 mg (2.92 mmol) of 3-chlorophenylhydrazine hydrochloride are added and the mixture is stirred for 48 hours at room temperature. The reaction mixture is concentrated by evaporation to approx. 5 ml and the precipitated solid is collected by suction filtration. After drying the crystals, they are taken up in 15 ml of acetic acid and stirred for 12 hours under reflux. The mixture is added to ethyl acetate, and washed with water, a saturated sodium bicarbonate solution and a sodium chloride solution. The organic phase is dried over sodium sulfate and concentrated on a rotary evaporator. The residue obtained is purified on a silica gel flash (mobile phase: cyclohexane/ethyl acetate 3:1) and then crystallized from diethyl ether/pentane. 528 mg (1.5 mmol, 62% yield of theory) of product are obtained.

Provenance & Evidence