N-Carbethoxyphthalimide → 2-[2-(5-ethyl-2-methoxy-6-methylpyridin-3-yl)ethyl]-2,3-dihydro-1H-isoindole-1,3-dione

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Reaction Steps

To a solution of crude 2-methoxy-3-(2-aminoethyl)-5-ethyl-6-methylpyridine (332 mg) in ethanol (7 mL) was added N-(carbethoxy) phthalimide (406 mg, 1.85 mmol). After stirring at ambient temperature for three hours the solvent was evaporated and the residue was chromatographed on silica gel by gradient elution with 20-100% ethyl acetate/hexane. The appropriate fractions were combined, the solvent evaporated and the residue triturated with hexane as the product slowly crystallized out to yield 202 mg of pure product, m.p. 77°-79° C.

Provenance & Evidence