Synthesis
The general procedure for the synthesis of 3-amino-3-(2-naphthalenyl)propionic acid from malonic acid and 2-naphthaldehyde was as follows: a mixture of 2.40 g of 2-naphthaldehyde (1-15 mmol), 2.44 g of malonic acid, and 3.54 g of ammonium acetate (molar ratio 1:1.1:2.3) was dissolved in 200 mL of 1-butanol, and the reaction was carried out at reflux for 1.5-2 hr, until the cessation of the release of carbon dioxide gas. Upon completion of the reaction, the precipitate formed was filtered and washed sequentially with boiling 1-butanol (2 x 50 mL), boiling ethanol (2 x 50 mL) and 100 mL of water. The precipitate was dried at 80-100°C for 8-10 hours. The purity of the product was checked by thin layer chromatography (TLC) and the reaction yield was about 65-80%.
References
[1] European Journal of Medicinal Chemistry, 2018, vol. 156, p. 252 - 268
[2] Chemistry - A European Journal, 2006, vol. 12, # 7, p. 1855 - 1874
[3] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1952, p. 113,116
[4] Chem.Abstr., 1953, p. 2157
[5] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1952, p. 113,116
