Hydrochloric Acid → 3-{[1-napthylamino]methyl}-5-ethyl-6-methyl-2-(1H)-pyridinone

Participants

Reaction Steps

A mixture of 2-methoxy-3-{[1-naphthylamino]-methyl}-5-ethyl-6-methylpyridine (125 mg, 0.41 mmol) and pyridine hydrochloride (500 mg, 4.3 mmol) was warmed at 145°-160° C. for 20 minutes. The reaction mixture was then cooled, water added, and the mixture made acidic with dilute aqueous hydrochloride acid. The product was then extracted into chloroform. Chloroform extracts were concentrated and the residue flash chromatographed on silica gel eluting with 5% methanol/95% chloroform. Appropriate fractions were combined and evaporated. The residue was triturated with diethyl ether to give 18.9 mg (15%) of product, m.p. 165°-167° C.

Provenance & Evidence