Pyridine → HCID 87342601, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of N-hydroxyacetamidine (37 g, 0.50 mol) in DME (500 mL) was treated dropwise with pyridine (118.5 g, 1.50 mol) at room temperature under N2 gas atmosphere. The mixture was then cooled to 0° C. and ethyl malonyl chloride (113 g, 0.75 mol) added drop-wise. After stirring at 0° C. for 30 min, then the mixture was warmed to room temperature, quenched with water, separated, the aqueous phase was extracted with EtOAc. The combined organic extracts were washed with brine, dried, concentrated to dryness. The intermediate was purified by the flash chromatography on silica gel to afford ethyl 3-({[(1Z)-1-aminoethylidene]amino}oxy)-3-oxopropanoate as a colorless solid (20 g, 21%). 1H NMR (CDCl3) 5.00 (br s, 2H), 4.23 (q, J=7.2, 2H), 3.52 (s, 2H), 2.01 (s, 3H), 1.31 (t, J=7.2, 3H).

Provenance & Evidence