Ethyl cyanoacetate → HCID 178510524, compound

Participants

Reaction Steps

Triethylamine (3.06 mL, 21.98 mmol) was added to a mixture of 4-phenoxybenzaldehyde (3.96 g, 19.98 mmol), 1-(2-amino-2-oxoethyl)pyridinium chloride (3.45 g, 19.98 mmol) and ethyl 2-cyanoacetate (2.260 g, 19.98 mmol) in methanol (80 mL) at room temperature. The resultant yellow solution was stirred at room temperature for 15 h to give a suspension. The yellow solid was collected by filtration, washed with methanol (2×20 mL), toluene (2×20 mL), hexanes (2×20 mL) and dried under vacuum to give trans-3-cyano-6-oxo-4-(4-phenoxyphenyl)-5-(pyridinium-1-yl)-1,4,5,6-tetrahydropyridin-2-olate (7.00 g, 91% yield). MS (ES+) m/z: 384 (M+H); LC retention time: 2.472 min (analytical HPLC Method A).

Provenance & Evidence