Succinic anhydride → Butanoic acid, 4-(nonylamino)-4-oxo-

Participants

Reaction Steps

To a stirred solution of succinic anhydride (25.0 g, 0.25 mol) in 150 mL acetone was added dropwise 35.8 g (0.25 mol) of nonylamine. The addition of the amine required 15 minutes, with the acetone solution reaching reflux before the addition was complete. Five minutes after the end of addition, a precipitate formed and the reaction mixture quickly became thick with suspended solids. Following addition of the amine the reaction mixture was stirred at room temperature for 1 hr. The precipitated solid was collected by filtration and washed with cold acetone. Air drying afforded 48.5 g of 4-nonylamino-4-oxobutyric acid as white, fluffy crystals, mp 114°-115.5° C. Upon standing the filtrate deposited crystals which were collected by filtration, washed with cold acetone, and air dried to yield an additional 10.9 g of the acid, mp 114°-115.5° C. Total yield was 59.4 g (98% of theoretical).

Provenance & Evidence