Ethylamine → HCID 15227516, compound

Participants

Reaction Steps

A mixture of pyridine-4-carboxaldehyde (XI; 10.71 g, 0.1 mole) and ethyl amine (12.88 g of a 70% water solution, 0.2 mole) were stirred for 20 min. Cyclohexane (75 ml) was added and the mixture was refluxed for 16 hrs under a Dean-Stark trap. The mixture was then concentrated in vacuo. Ethanol (100 ml) and sodium borohydride (five 0.4 g tablets, 50 mmole) were then added to the residue and mixture was stirred for 3 hrs in an ice bath. The mixture was concentrated in vacuo and the residue was dissolved in acetonitrile (100 ml) and filtered. Acetic anhydride (10.38 ml, 0.11 mole) was added and the reaction was stirred for 2 days. Sodium carbonate (15.9 g, 0.15 mole) was added and the solution was refluxed for 20 min. The mixture was cooled and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed on silica gel using 5% methanol/ethyl acetate as the eluent to give the product (14.57 g, 82%).

Provenance & Evidence