Potassium Carbonate → HCID 59596629, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of ethyl 4-chloro-nicotinate (2.05 g, 11.0 mmol) and sarcosine ethyl ester hydrochloride (4.75 g, 30.9 mmol) in anhydrous DMF (40 ml), under an argon atmosphere, was added sodium hydride (59.6 mmol, 60% in dispersion oil, 2.39 g) in portions over 20 minutes. On complete addition the mixture was heated at 80° C. for 1.5 hours. Potassium carbonate (1.52 g, 11.0 mmol) was then added and the mixture heated for a further 2 hours. The reaction mixture was then quenched by the addition of water (50 ml) and subsequently concentrated to provide a residue. The residue was partitioned between ethyl acetate (100 ml) and water (100 ml). The layers were separated, the aqueous phase was cooled to 0° C. and the pH adjusted to 7 by the addition of concentrated HCl. The aqueous phase was aged overnight and the resulting precipitate was filtered, washed with water and dried under vacuum at 60° C. to give a white solid (700 mg, 15%). LCMS (method B): RT=1.82 min, M+H+=221.

Provenance & Evidence