Succinic anhydride → butanoic acid, 4-(butylamino)-4-oxo-

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Reaction Steps

n-Butylamine (9.05 g, 0.1225 mole) was dissolved in Et2O (30 ml). Succinic anhydride (5 g, finely powdered) was added portionwise. After addition was complete, the heterogeneous mixture was stirred 1 hour at room temperature. The reaction mixture was then poured into 10% NaOH in H2O (10 ml) and Et2O (30 ml). The layers were separated and the ether layer was extracted with additional 10% NaOH (10 ml). The combined aqueous layers were washed with ether (30 ml) and acidified with concentrated HCl to give a layer of oil above the water layer. This was extracted with Et2O (50 ml×2). The ether extracts were washed with saturated NaCl solution (3×30 ml) and dried (MgSO4). The solvent was removed in vacuo to give a white solid (7.5 g) which was recrystallized from benzene to give title acid as needle shaped crystals (4.83 g, 56%), m.p. 93.5°-94.5° C.

Provenance & Evidence