Hydrochloric Acid → HCID 86600617, compound

Participants

Reaction Conditions

Reaction Steps

4-Trifluoromethyl aniline (0.97 g, 6.0 mmol) was gradually added to acetic acid (3.5 ml), water (1.7 ml) and concentrated hydrochloric acid (1.7 ml) and dissolved, and cooled to 5° C. A solution of sodium nitrate (0.5 g, 7.2 mmol) in water (2 ml) was gradually added thereto at a temperature of 10° C. or less. The resulting solution was gradually added to a mixture of N-(6-chloro-3-pyridylmethyl)-2-cyanoacetic acid amide (1.3 g, 6.0 mmol), sodium acetate (1.23 g, 15.0 mmol), ethanol (30 ml) and 1N aqueous solution of sodium carbonate (40 ml). After stirring at room temperature for 5 hours, water and ethyl acetate were added thereto and subjected to extraction. The organic phase was washed with a saturated brine, and dried on anhydrous sodium sulfate. The residue obtained by filtering and concentrating was purified with a silica gel chromatography to obtain N-(6-chloro-3-pyridylmethyl)-2-cyano-2-(4-trifluoromethylphenyl hydrazono) acetic acid amide (Compound No. 184) (0.12 g, 0.30 mmol, 5%) (Compound No. 185) (1.15 g, 3.00 mmol, 50%). Geometrical isomerism (E/Z) was not determined.

Provenance & Evidence