Phenylacetyl chloride → HCID 10901406, compound

Participants

Reaction Steps

A mixture of ethyl 1,4-dihydro-4-oxo-3-phenyl-5-pyridinecarboxylate (prepared from phenylacetyl chloride according to the procedures described in J. Org. Chem. 1978, 43, 2087-2088 and J. Heterocyclic Chem. 1980, 17, 359-368) (3.82 g, 15.7 mmol) and phosphorus oxychloride (50 ml) was heated at reflux overnight. The excess solvent was removed in vacuo. The residue was partitioned between ice-cold aqueous Na2CO3 and ethyl acetate, and the organic layer was evaporated in vacuo to afford 3.72 g (90%) of the title compound as a brown solid; 1H NMR (250 MHz, CDCl3) δ1.44 (3H, t, J 7.2 Hz), 4.47 (2H, q, J 7.2 Hz), 7.40-7.54 (5H, m), 8.62 (1H, s), 8.91 (1H, s); MS (ES+) m/z 262/264 [MH]30 .

Provenance & Evidence