Sodium Carbonate → (1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)(phenyl)acetic acid

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Reaction Steps

To a stirred mixture of phenylglycine (3.0 g, 20 mmoL) and sodium carbonate (2.23 g, 21 mmoL) in 450 mL of water is added N-carbethoxyphthalimide (4.38 g, 20 mmoL). After 45 minutes, the reaction slurry is filtered. The filtrate is stirred and the pH adjusted to 1-2 with 4N hydrochloric acid. After 1 hour, the resulting slurry is filtered and the solid washed with water. The solid is dried in vacuo (60° C., <1 mm) to afford 2.88 g (51%) of α-phthalimidophenylacetic acid, which can be alternatively named as N-phthaloylphenylglycine, as a white powder.

Provenance & Evidence