Acetic Acid → Ethyl 4-[(1-chloro-2-naphthyl)amino]-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylate

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Reaction Steps

Ethyl 6-chloro-4-[(1-chloro-2-naphthyl)amino]nicotinate was dissolved in CHCl3 and reacted with Me2SO4, followed by triethylamine, AcOH and EtOH as described for example 33, step B. Purification by flash chromatography on silica gel (50% EtOAc/Hexane) afforded ethyl 4-[(1-chloro-2-naphthyl)amino]-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylate (71%). 1H NMR [400 MHz, (CD3)2SO] δ 9.73 (s, 1H), 8.59 (s, 1H), 8.18 (d, J=8.4 Hz, 1H), 8.02 (t, J=8.4 Hz, 2H), 7.75-7.69 (m, 2H), 7.64-7.59 (m, 1H), 5.59 (s, 1H), 4.34 (q, J=7.1 Hz, 2H), 3.45 (s, 3H), 1.35 (t, J=7.1 Hz, 3H).

Provenance & Evidence