2-(2-Chlorophenyl)glycine

Description

Uses

reaction suitability

Synthesis

143-33-9

89-98-5

86169-24-6

The general procedure for the synthesis of (R)-2-amino-2-(2-chlorophenyl)acetic acid from sodium cyanide and o-chlorobenzaldehyde was as follows: 2-chlorophenylglycine was prepared according to the method described in Scheme 1. O-chlorobenzaldehyde (2-chlorobenzaldehyde), ammonium bicarbonate (NH4HCO3, 23.7 g) and sodium cyanide (NaCN, 14.7 g) were dissolved in a mixed solvent of 500 ml of methanol and 500 ml of water, and the reaction was stirred for 5 hours at 65-70 °C. Upon completion of the reaction, the solution was concentrated and transferred to an autoclave, where 45% sodium hydroxide (NaOH) solution was added and refluxed at 120°C for 4 hours. After the reaction mixture was cooled, 2 g of activated carbon was added and stirred for 10 minutes for decolorization. The activated carbon was removed by filtration and the pH of the filtrate was adjusted to 7-8 with 50% sulfuric acid (H2SO4). the precipitate was collected by filtration and washed with water to give 27 g (58% yield) of 2-chlorophenylglycine. The product was RS-2-chlorophenylglycine with a specific optical rotation of +0.16 (C=1, 1N HCl) and a melting point of 185.4-186.8 °C. The product was a mixture of RS-2-chlorophenylglycine, RS-2-chlorophenylglycine and RS-2-chlorophenylglycine.

References