Succinic anhydride → 4-Oxo-4-{[2-(pyridin-2-yl)ethyl]amino}butanoic acid

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Reaction Steps

To a solution of 5.0 g (50 mmol) of succinic anhydride in 50 mL of dichloromethane was added 550 mg of DMAP and 6.1 g (50 mmol) of 2-(2'-aminoethyl)pyridine. An exothermic reaction resulted. The reaction was refluxed for 1 h and cooled to room temperature and stirred for 48 h. The reaction is worked up by concentrated in vacuo; the resulting solid was dissolved in pH 4 buffer and extracted three times with 4:1 ethyl acetate/tetrahydrofuran after the aqueous solution had been saturated with ammonium sulfate. The organic layer was dried over sodium sulfate and concentrated in vacuo to give a residue. The residue was recrystallized from ethyl acetate/methanol to give 5.5 g (50%) of 4-oxo-4-[[2-(2-pyridinyl)ethyl]amino]butanoic acid.

Provenance & Evidence