Malonic Acid → 3-Amino-3-(pyridin-3-yl)propanoic acid

Participants

Reaction Conditions

Reaction Steps

The reaction flask was charged with 300 g (264.3 mL)(2.8 mol) of cold 3-pyridine carboxaldehyde and 60 mL of absolute ethanol. A reaction temperature of 13° C. resulted. With good stirring, 291.36 g (2.8 mol) malonic acid was added in one portion (solid addition) over about 2 min, followed by 90 mL ethanol. Immediately following this addition, 323.73 g (4.2 mol) ammonium acetate was added over about 10 min (solid addition), followed by 250 mL ethanol. During this addition, the reaction cooled to about 38° C. The bright orange mixture was heated to and maintained under gentle reflux for 5 h. The heating mantle was removed, and the mixture was allowed to cool to ambient temperature overnight. The solid was collected by suction filtration (50 min) and washed with 400 mL methanol (30 min). The filtercake was washed with a second portion of 200 mL methanol (10 min). The filtercake was partially dried under suction for about 60 min. The solids were dried in vacuo at 35-40° C. to constant weight (38 h) to yield 303.38 g (65.2%) 3-amino-3-(3′-pyridyl)propionic acid as a white powder.

Provenance & Evidence