Ethanol → HCID 19987387, compound

Diethyl acetamidomalonate (20.0 g, 0.921 mol) is dissolved in 200 mL of absolute ethanol. Sodium metal (4.2 g, 0.1827 mol) is added and the mixture is stirred at room temperature until all of the metal is dissolved. The solution is cooled to 0-5° C. and 13.3 g (0.0811 mol) of 4-picolyl chloride hydrochloride in 100 mL of absolute ethanol is added rapidly. After stirring at room temperature overnight, the mixture is filtered through celite and the filtrate concentrated to a dark oily solid. The residue is dissolved in 200 mL of concentrated hydrochloric acid and refluxed for 4 hours and concentrated in vacuo to a dark oily solid. The residue is dissolved in 200 mL methanol and 2 mL of concentrated hydrochloric acid and refluxed overnight. The solution is concentrated to 16.7 g of orange solid. The hydrochloride salt is purified by trituration with ethanol and ethyl acetate to yield the title compound of a pale yellow solid; mp 180-182° C.

1. dissolutionis dissolved
2. temperatureThe solution is cooled to 0-5° C.
3. stirringAfter stirring at room temperature overnight
4. filtrationthe mixture is filtered through celite
5. concentrationthe filtrate concentrated to a dark oily solid
6. dissolutionThe residue is dissolved in 200 mL of concentrated hydrochloric acid
7. temperaturerefluxed for 4 hours
8. concentrationconcentrated in vacuo to a dark oily solid
9. dissolutionThe residue is dissolved in 200 mL methanol
10. temperature2 mL of concentrated hydrochloric acid and refluxed overnight
11. concentrationThe solution is concentrated to 16.7 g of orange solid
12. customThe hydrochloride salt is purified by trituration with ethanol and ethyl acetate

ORD record

ord-2790eb44df42406089c2b1b4e851bc45

Source dataset

uspto-grants-1991_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05066662