Pyridine → HCID 23353317, compound

Participants

Reaction Conditions

Reaction Steps

2-Cyano-3-hydroxypyridine (1.2 g, 10 mmol), prepared as described in Synthesis 316 (1983), was aedded in portions to a 0° C. suspension of NaH (0.4 g of 60% dispersion, 10 mmol) in DMF (5 mL). After stirring for 20 min at 0° C., ethyl bromoacetate was added dropwise. The reaction was stirred for 30 min at 25° C. and was the poured into ice water. The resulting solid was collected by filtration and was washed with a small portion of water. The crude ethyl ester was taken up in EtOAc, dried (MgSO4), filted, and concentrated (1.16 g obtained). To the pyridine (1.0 g, 5.0 mmol) in THF (20 mL) was added potassium t-butoxide (0.56 g, 5.0 mmol). After stirring for 45 min, the reaction was partitioned between EtOAc and NaHCO3 solution. The layers were seperated and the aqueous layer was extracted with EtOAc (2x). The combined organic layers were washed with brine, dried (MgSO4), filtered, and concentrated to provide 0.76 g (76%) of the title compound: 1H NMR (300 MHz, CDCl3) δ1.46 (t, 3H), 4.47 (q, 2H), 5.21 (bs, 2H), 7.38 (dd, 1H), 7.76 (dd, 1H), 8.56 (dd, 1H).

Provenance & Evidence